Vacation Rentals By Owner In Monterey, MA

$290.32

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey, Massachusetts, United States

Get carried away to this quaint 3-bedroom, 1-bath vacation rental in beautiful Monterey, Massachusetts. Surrounded by scenic landscapes, this cozy cottage is the perfect place to rest and recharge. Spend your days enjoying water sports from the private dock, hiking the Appalachian Trail, or taking a scenic drive to the town of Great Barrington. In the evenings, relax on the deck and fire up a feast. Immerse yourself in the natural beauty and serenity of the Berkshires at this delightful home!brbr-- THE PROPERTY --brbrMassTaxConnect ID C0467761930 | Walk to Private Boat Dock | Free WiFi | Washer & Dryer | Near Outdoor RecreationbrbrBedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Additional Sleeping: Pack ‘n PlaybrbrOUTDOOR LIVING: Spacious deck, screened-in porch, gas grill, dining area, 2 kayaks, beach towels, fire pit (wood not provided)brINDOOR LIVING: Open layout, Smart TVs, breakfast bar, fireplace (decorative)brKITCHEN: Refrigerator, microwave, stove/oven, dishwasher, cooking basics, dishware/flatware, coffee maker, trash bags/paper towels, toaster oven, CrockpotbrGENERAL: Linens/towels, split A/C unit (living room), complimentary toiletries, hair dryerbrFAQ: Single story, steps required to accessbrPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrSUN & SAND: Lake Garfield Boat Dock (0.2 miles), Lake Garfield Beach (2 miles), Otis Town Beach (9 miles), Lenox Town Beach (13 miles), Sandy Beach at Laurel Lake (13 miles) brWILD & FREE: Bidwell House Trails (3 miles), Diane's Trail Trailhead (4 miles), Beartown State Forest (6 miles), Tolland State Forest (13 miles), Monument Mountain Reservation Parking (14 miles), Otis State Forest (14 miles), Granville State Forest (18 miles)brMONTEREY MUST-SEES: Bidwell House Museum (3 miles), Norman Rockwell Museum (16 miles)brREEL IT IN: Berkshire Rivers Fly Fishing (12 miles), Trout Pond View (13 miles), Berkshire Bass Tackle Store (15 miles) brAIRPORT: Bradley International Airport (39 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This single-story property requires steps to accessbr- NOTE: The fireplace and hot tub are unavailable for guest use

Bed

Bath

Sleeps

$647.06

/ Nightly

Private Vacation Home

Light, Airy And Fabulous

Monterey, Massachusetts, United States

This is a special place and it’s 3 minutes to Lake Garfield and 12 minutes to Butternut Ski Area! It's a very pretty and comfortable home. High vaulted ceilings with 3 Bedrooms and lots of windows so trees and green are seen from every angle. Peaceful and serene, it will make you happy.brbrLarge master bedroom on main floor with large 2-part private bath with stand-up shower and Jacuzzi tub. 2 upstairs bedrooms (one with queen bed other with daybed - 2 twins). All rooms are nice size with space to move around. Two full baths and an extra half-bathroom - right off the kitchen. Great room with a working cast iron stove and Mitchell gold sectional sofa that looks out on the meadow. The kitchen is well stocked with fiesta ware and large pots and serving dishes. Located on a quiet country road with two porches overlooking garden and meadow. The house has deeded rights to the lakefront including a private dock, swimming dock and kayaks. The popular Monterey Beach is 1 mile down the road. 10 minutes to the Lee outlets, 12 minutes into Great Barrington and 25 minutes to Tanglewood and Lenox and Jacobs Pillow. Very clean, neat and organized. Every thing is easy at Hopping Hupi.

Bed

Bath

Sleeps

$228.19

/ Nightly

Cottage

nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Monterey, Massachusetts, United States

Sweet, newly renovated cottage, in a blissfully tranquil setting on Lake Garfield in Monterey, MA. Secluded, private, yet close to amenities, the cottage sits on a secluded 9 acre wooded lot along with one other house. 100yd walk to the private dock (shared with the other house). Monterey is at a higher elevation in the Berkshires (above Great Barrington), so the air is cool and refreshing during most of the summer. The cottage has been completely renovated and is equipped with WiFi and air conditioning. New, open-plan kitchen has full range of appliances, including dishwasher. Full-size front loading washer and dryer. Living room contains a plush L-shaped sofa, flat-screen TV/DVD player with Direct TV package, wood burning stove, and lounge chairs. Indoor and outdoor dining areas. Workspace with desk and bookcase. The master bedroom has a queen bed with high quality gel mattress, antique dresser and antique wardrobe. The spare bedroom has a queen on bottom/full on top/combination bunk bed, also fitted with high quality gel mattresses. Large porch with dining and lounging seating. Overhead fan and baseboard heat. Linens, blankets, pillows and towels provided. Outdoor lounge chairs, fire pit, propane BBQ grill, and x-large 2-person hammock. One Canoe and two kayaks. brbrA 15 minute walk from the cottage is the village of Monterey, MA. Dotted with pre-colonial buildings, it is a hidden jewel in the Berkshires. Within walking distance there is an honesty farm stand where you can get the freshest veggies, as well as a farm that produces goat cheese from their own herd. Monterey is home to the historic Bidwell Museum. Monterey is a 20 minute drive from Great Barrington, where you can find a large variety of restaurants, grocery stores, theaters and shops. In addition, all the attractions of Great Barrington and the Berkshires are at your fingertips: Tanglewood, Kripalu Yoga Center, Norman Rockwell Museum, Hancock Shaker Museum, the Clark Museum, the WE DuBois Museum and the Naumkeag Museum. brNatural beauty abounds. The Appalachian Trail is nearby for hikers, and beautiful back-country roads are here for bikers. Your neighbors will include owls, eagles, herons, ducks, and possibly a curious baby bear (please don’t leave food outside!). A perfect, soothing get-away. brbrbrCottage Featuresbrbr- Approximately 1,275 sq ft. Sleeps up to 5br- 1 queen bed in master bedroom. 1 queen bed/1 full bed (bunk) in second bedroom. br- Extremely comfortable gel mattressesbr- Covered porch with sitting and eating areasbr- Indoor and outdoor dining areasbr- Propane BBQ grill with accessoriesbr- Air conditioningbr- Wood-burning stovebr- X-large 2 person Hammockbr- Outdoor lounge chairs with fire pitbr- Fully equipped kitchen with new appliances. Full size range and refrigerator. Microwave and dishwasher. Toaster oven, basket type #2 and individual pod coffee makers, electric water kettle, blender. High quality pots and cooking utensilsbr- Full size front-loading washer and dryerbr- TV with DVD and Direct TV packagebr- 900MHz speed Internetbr- Fansbr- Linens, bath towels and beach towels providedbr- Hair dryerbr- Landline phonebr- Private dock (share with main house)br- Dogs under 20 pounds allowed. $150 cleaning feebr brA note concerning cellphone reception. We are in a natural area, so cellphone reception may be limited to texting. Alternatively you can use WhatsApp or the landline for local voice calls.

Bed

Bath

Sleeps

$562.05

/ Nightly

Private Vacation Home

Garfield Grounds | Lakeside • Guest Cottage • Dock

Monterey, Massachusetts, United States

Welcome to one of the best lakeside spots in The Berkshires! This spacious house features a stunning private dock perfect for swimming and vast open grounds ideal for entertaining. Enjoy the cozy fireplaces and send the kids over to the guest house for movie time, which sleeps 2 and includes its own wood stove. With an open floor plan on the main level and a spacious TV room in the basement, this property is the perfect retreat for family and friends to create unforgettable memories together!brbr✔ Private dockbr✔ Separate Guesthouse (4th bedroom: only included in the booking from Memorial Day Weekend through Columbus Day Weekend)br✔ Jacuzzi tubbr✔ High-speed Wi-Fibr✔ Smart TVbr✔ Fully equipped kitchenbr✔ Washer & dryerbr✔ Free parkingbr✔ Air conditioningbr✔ Pack n Play Travel Crib (Upon request)brbr➥ LAKEFRONTbr➥ 8 mins to Beartown State Forestbr➥ 13 mins to Ski Butternutbr➥ 18 mins to The Mahaiwebr➥ 20 mins to The Berkshire Theatrebr➥ 20 mins to The Lion`s Denbr➥ 20 mins to Tanglewoodbr➥ 20 mins to Shakespeare and Co.br➥ 20 mins to Jacob`s Pillowbr➥ 20 mins to Great Barringtonbr➥ 21 mins to W.E.B. Du Bois National Historic Sitebrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 3 bathrooms, all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 2 Single bedsbrBedroom 2 - 1 King bedbrBedroom 3 - 1 Queen bedbrShared Space - 1 Murphy bed in the cabinbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified. brbrThere is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months. brbrPlease note that the cottage (4th bedroom) is only available from Memorial Day through Columbus Day. We shut this down and winterize during the colder months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

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Bath

Sleeps

$364.62

/ Nightly

Private Vacation Home

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey, Massachusetts, United States

Nestled on picturesque grounds, this modern and updated 3-bedroom home offers the perfect blend of comfort and luxury. Enjoy al fresco dining or simply relax on the expansive deck, taking in the stunning wooded views.brInside, the home boasts a large gourmet eat-in kitchen with top-of-the-line appliances, a formal dining room for entertaining, and a spacious living room that invites warmth and relaxation. The newly renovated bathroom features a heated floor and skylight, adding a touch of spa-like elegance.brOutdoors, a cozy fire pit area provides a perfect spot for evening gatherings, while the wrap-around driveway offers convenience and accessibility. Located near many of the Berkshires' most popular attractions, this property is a true gem.

3

Bed

1

Bath

6

Sleeps

$973.58

/ Nightly

Private Vacation Home

Waterfront: 4 bedroom home on Lake Buel with Gorgeous Sunsets, Sleeps 8!

Monterey, Massachusetts, United States

Immaculate Waterfront Lake House with Direct Access to Lake Buel. This charming, spotless, 4-season lake cottage is perched on a small hill with lovely views of Lake Buel, which is a wonderful lake for swimming, boating, kayaking, jet skiing, skating and ice fishing - weather permitting. brbrSweetwater Amenities include: 4 bedrooms, 2 full baths - main floor bedroom and full bath - high speed fiber WIFI internet and good cell service, 2 HDTV Smart TVs with streaming channels like Netflix, Hulu, and Prime video, mini split AC throughout, all stainless appliances: range, freezer/fridge, dishwasher, microwave, coffee maker, toaster, blender, washer/dryer, stunning sunroom bar and media room, wood burning stove, blue stone terrace with outdoor seating, umbrella and a propane grill. There are 2 docks, 1 canoe, and 4 kayaks for guest's use, plus outdoor fire-pit with seating. Located less than 10 minutes to the center of Great Barrington and less than 5 to Ski Butternut, Sweetwater cottage is well appointed and available for all seasons! (No smoking, and please inquire about well trained pets which will be considered on a per pet basis. Pets fees will apply.)brbrThis open concept lake cottage has a wall of windows to take in the views. The main floor hosts the kitchen, dining, 4 season sunroom with bar and media room, main floor bedroom, a full bathroom, and laundry. The kitchen has every gadget and gleaming stainless appliances: freezer/fridge, electric range, dishwasher and microwave + Keurig coffee maker, toaster, and blender. The kitchen has a large Island and a dining room with beautiful lake views. This area also has a wood stove and large Smart TV with access to all your streaming channels. Just off the dining room is the sunroom with a bar, stools, sofa, club chair and another large HD Smart TV. The room has beautiful views of the lake and has cozy seating as well. There are mini split wall units, throughout the house which provide both AC and supplemental heat, as needed. The main floor, primary bedroom, has a queen bed, TV, and also has lake views. The full bathroom, also located on the main floor, with a tub/shower and a washer/dryer. brbrThe second floor has 3 more guest bedrooms, which all share a full bath. This bathroom has a brand new walk-in, glass shower. Guest bedroom #2 has a queen bed, Guest room #3 has 2 twin beds with lake views, and Guest room #4, also with lake views, has a full bed.brbrOutside, guests enjoy the blue stone terrace with outdoor seating, sun umbrella, and propane grill. A blue stone pathway leads from the back patio, past the fire-pit area (with additional seating) down to the waterfront. There is a large, lush lawn perfect for outdoor games, picnicking, or sun-bathing. Guests have access to 2 docks as well as the 4 kayaks and a canoe - so fun!brbrPlease note that Lake Buel does permit speed boats. Please inquire for information about boat or jet ski rentals. Sweetwater Cottage is less than 10 minutes to the center of Great Barrington and Ski Butternut is less than 5 minutes. Leaf peeping on a kayak is epic on the lake, and fall weekends are available! brbrLocated less than 10 minutes to the center of Great Barrington, and less than 5 to Ski Butternut, Sweetwater cottage is a terrific rental any time of the year! brbrNo Smoking and please inquire about pets. An additional pet fee will apply.

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Sleeps

$1270.59

/ Nightly

Private Vacation Home

Fabulous Renovated Log Cabin: the perfect getaway with new pickleball court!

Monterey, Massachusetts, United States

Stunning log cabin in the Berkshires on 10 private wooded acres complete with brand new 4 season hot tub, in-ground pool with electric cover, gorgeous pickleball and basketball court, stunning fire pit perfect for s'mores, relaxing hammock, stocked veggie garden, private outdoor shower, new built in grill, tons of indoor and outdoor games, beautiful screened in porch, stocked gourmet kitchen, radiant heated floors, huge family room with fireplace, finished basement with billiards, darts and big screen TV. 3 gorgeous bedrooms, 3 big bathrooms with beautiful tile work and heated floors, and even 2 extra twin beds downstairs. This is a great getaway from the hustle/bustle. Right near the lake, skiing, town of Great Barrington with great stores and restaurants, Tanglewood, Stockbridge, Lenox, Butternut, theaters, and more. Relax and enjoy! It's all new, furnished and has everything you need for a perfect getaway with just family or with friends from afar.

Bed

Bath

Sleeps

$710.09

/ Nightly

Cottage

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

Monterey, Massachusetts, United States

Enjoy this very private, super comfortable, 1925 lake cottage, waterfront boathouse and dock for an entire Berkshire Summer Season. There are three bedrooms and an office that may be used for spillover, and also the large screened porch facing the lake. The boathouse has a twin futon bed, and it's the most magical place to wake up. Located on a private road with almost three acres of serenity.

Bed

Bath

Sleeps

$538.39

/ Nightly

Private Vacation Home

Beautiful Berkshire family home

Monterey, Massachusetts, United States

This is a beautiful 5 bedroom Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads, 12 mins to Butternut Family Skiing & fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood.brbrThe SpacebrThe large comfortable house has 5 good size bedrooms with a private room downstairs with its own sleeping quarters, WC and living area with separate bedroom off it. Excellent kitchen and dinning areas with deck dinning, screened porch dinning and large garden table to fit 8+. It's very family friendly (well behaved dogs & cats welcome) with swings for the kids. The house was built in 2006 and has excellent insulation - It's cool in summer and warm in winter. There is WIFI through out house and in the garden, even on the hammocks!brbrThe famous Tanglewood and Jacobs Pillow are within 25 minutes and the area is rich in entertainment for all ages and very family friendly. 15 minute drive to skiing and the Appalachian trail is only a 10 min drive too if you fancy a long walk.brbrEven though you feel completely private, this house is only 5 minutes to the local village with the famous Monterey general store selling local food produce and the town beach for swimming, boating and fishing lake. In the winter we're only 15 minutes from the wonderful family friendly ski mountain of Butternut. brbrHistoric Great Barrington is only 20 minutes drive with many excellent local restaurants and shops, farmers markets + local food stores. A Guidos and Big Y's are within 20 mins drive for all your grocery needs.brbrThe house has 5 bedrooms and beds for 10 people, 3 x queens & 4 x twins, but there are 2 twin air beds + 1 queen bed for extra people to stay. Accommodating up to 12 people comfortably. brbrA cathedral living room with windows up to the 30 foot ceiling, an English farm house dinning table seating up to 8, a French velvet sofa, a large wood burning stove as well as a spacious kitchen with Whirlpool large fridge and Bosch dishwasher. Two bathrooms one with a roll top bath and two showers plus a guest toilet. There is also a large screened porch for summer dining and entertainment.brbrDownstairs is a private 700 sq ft family room which opens onto the garden; with two separate bedrooms with queen size beds and a separate living room with original Danish furniture. One bedroom has its own third toilet. This is a great family area. brbrThere is a washer/dryer downstairs plus a drying room for, swim towels, ski clothes and a shed to store skis. The AC is a portable cooling system. brbrPlease note that we only have internet enabled TV, Roku which provides Netflix and Amazon Prime and other internet cable services if you have a subscription. brbrMore reviews here:

Bed

Bath

Sleeps

$590.41

/ Nightly

Private Vacation Home

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Monterey, Massachusetts, United States

The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only a few minutes walk to the town's beach with life guards on site. This one-level modern home has vaulted ceilings throughout. There are two master suites with king beds and two other bedrooms with queen beds. A walk out deck from one of the master bedrooms so you can enjoy morning coffee. Three common spaces include a loft for guests to chill out. A new washer and dryer is in one of the guest bathrooms. The kitchen with new stainless steel appliances is equipped with premium cooking tools and pots. Guests can hang out at the kitchen counter bar stools while someone is preparing meals. A gas grill is available on the front deck which can be accessed from the kitchen or the great room. There are two gas fireplaces to keep you cozy at night time.brbrIn the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about 10 minute drive. Monterey is a small secluded town with one general store, the Bidwell Museum and a few small farms where you can get fresh milk, eggs, pork, chicken, maple syrup, goat cheese, fruits and vegetables. It is only a 15 minute drive to Great Barrington where local gift shops, organic grocery stores and farm-to-table and gastronomic restaurants are located. If you like shopping, Lee Premium Outlets is 15 minutes away.

4

Bed

4

Bath

10

Sleeps

$549.88

/ Nightly

Cabin

Misty Pines Cabin | Wood Stove • Sauna

Monterey, Massachusetts, United States

Welcome to Misty Mountain Camp — a cozy 3-bedroom, 3-bath escape surrounded by peaceful woods and Berkshire charm. Enjoy nearby adventures at Beartown State Forest, Lake Garfield, Steadman Pond, and Greene Park, or explore local history at the Bidwell House Museum. After a day outdoors, relax on the deck, unwind by the fire pit, and soak in the quiet beauty of nature. The perfect getaway for families, friends, and nature lovers alike.brbr✔ High-speed Wi-Fibr✔ Smart TVbr✔ Fully equipped kitchenbr✔ Coffee makerbr✔ Washer & dryerbr✔ Free parkingbr✔ Outdoor wood-fired saunabr✔ Indoor fireplacebr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr➥ 5 mins to Lake Garfield Beachbr➥ 9 mins to Beartown State Forestbr➥ 13 mins to Ski Butternutbr➥ 18 mins to The Mahaiwebr➥ 21 mins to W.E.B. Du Bois National Historic Sitebr➥ 22 mins to The Lion`s Denbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Queen bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 4 Twin bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified. brbrThere is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Bed

Bath

Sleeps

$312.42

/ Nightly

Agritourism

Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Monterey, Massachusetts, United States

Escape to a renovated barn that blends rustic charm with modern comfort. Enjoy airy, open spaces with vaulted ceilings and exposed beams, cozy living areas, and a small kitchenette. Relax in the open living room or unwind out on the patio. Outside, soak up peaceful views, sip a morning coffee, or stargaze at night. Perfect for a quick getaway or an extended stay, this serene barn offers a cozy escape from daily life—an ideal spot to recharge, reconnect, and create lasting memories.brbr✔ Self check‑inbr✔ Fully equipped kitchenbr✔ Outdoor grill & spacious patiobr✔ High-speed Wi‑Fibr✔ Writer`s Nookbr✔ Air conditioningbr✔ Free parking on premisesbr✔ Pet-friendlybr✔ Toiletries and Bathroom essentialsbr✔ Pack n Play Travel Crib (Upon request) brbr➥ 2 mins to Lake Garfield town beachbr➥ 9 mins to Beartown State Forestbr➥ 14 mins to Butternut Ski Areabr➥ 18 mins to The Mahaiwebr➥ 26 mins to Norman Rockwell Museumbr➥ 28 mins to Tanglewoodbr➥ 31 mins to Catamount Ski Area brbr✦BEDS & BATHS✦brInside we have 2 bedrooms and 1 bathroom, all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bed and 1 Twin bunk beds brbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.`brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 1 dog. No other types of animals are authorized. brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified.brbrThere is space for parking two cars in the driveway. Please note, the road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brbr**There is no lake access directly from the barn, but the town beach is just 2-3 minutes away by car. The barn shares more than an acre of charming New England landscape with an adjacent owner’s main house, surrounded by trees on three sides

Bed

Bath

Sleeps

$668.4

/ Nightly

Private Vacation Home

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Monterey, Massachusetts, United States

Summary:brbrNestled into more than 8 acres of pristine, private forest above the northwest section of Lake Garfield in Monterey, Hupi House blends classic New England farmhouse architecture with contemporary amenities. This serene retreat is a quick drive to nearby towns and the best outdoor activities the Berkshires have to offer, but far enough away to provide tranquil privacy. Whether you’re here with family or friends, for vacation or a work getaway, you’ll find everything you need in this cozy home.brbrbrbrThe Space:brbrThis 2,700-square foot house is perfect for families or friends seeking to get away from it all. With two, distinct private bedroom areas separated by the main floor, adults and kids (or families with young children) can all enjoy their own experience. Adults can find peace and quiet in the top floor suites, which consist of separate king and queen bedrooms; the lower level features a king bedroom, and a kids bedroom with two, twin bunk beds that can sleep a total of four. Each bedroom area has its own full bathroom; the house also features an additional full bath on the main floor, for additional privacy and convenience. All bedrooms feature comfortable memory foam mattresses and crisp white sheets from Brooklinen.brbrbrbrThe main floor is ideal for group gatherings with a large foyer, a recently remodeled kitchen, a screened-in patio with a cozy breakfast table, separate dining room, and a spectacular living room with a fireplace, books galore, and stunning views of the forest and mountains beyond. brbrbrbrOther amenities include recently refinished wood floors, state-of-the-art mini-split air conditioning, ultra-fast WiFi with a fiber optic connection, a cozy den with a 55-inch television connected to a Roku sound bar, washer and dryer, and a Weber charcoal grill.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrGuest Access:brbrThe entire house is reserved for your enjoyment. If there is anything you need during your stay we are available via phone or your booking channel!brbrbrbrThe Neighborhood:brbrThe house is nestled into a tranquil, wooded hill above Lake Garfield: enjoy easy, un-trafficked walks along Hupi Road toward Beartown State Forest, or hikes through the woods on the property to the secluded pond down below. The town beach on Lake Garfield is just a five minute stroll from the front door and the charming village of Monterey with its general store and post office is only a mile away. Enjoy family skiing at Butternut (a 10-minute drive), shopping and dining in Great Barrington (a 15-minute drive), or the outstanding cultural offerings, parks, and restaurants in the southern Berkshires region. We provide plenty of recommendations in our house guide.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying and no pets allowed and being respectful of the neighbors apply.brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

Bed

Bath

Sleeps

$570.81

/ Nightly

Private Vacation Home

Bidwell Landing | Lakefront • Spacious

Monterey, Massachusetts, United States

Enjoy this spacious 4 bed, 4 bath home nestled on Lake Garfield in the beautiful Berkshires. Well-curated, clean, and perfect for entertaining, with expansive outdoor decks on multiple levels. Surrounded by pine forest and overlooking the lake, the property features a stunning dock, creating an ideal retreat for family and friends. A serene, nature-filled escape with luxurious comfort and breathtaking views all just a short drive from Great Barrington, Smithsonian`s #1 small town in the country.brbr✔ Lake viewbr✔ Private Dockbr✔ High-speed Wi-Fibr✔ Smart TVbr✔ Fully equipped kitchenbr✔ Outdoor Grillbr✔ Washer & dryerbr✔ Free parkingbr✔ Heating & air conditioningbr✔ Pack n Play Travel Crib (Upon request)brbr➥ 5 mins to Lake Garfield Beachbr➥ 8 mins to Beartown State Forestbr➥ 13 mins to Ski Butternutbr➥ 18 mins to The Mahaiwebr➥ 21 mins to W.E.B. Du Bois National Historic Sitebr➥ 23 mins to Berkshire Theatrebr➥ 26 mins to Norman Rockwell Museumbrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 King bedbrBedroom 3 - 1 QueenbrBedroom 4 - 2 Full bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified. brbrThere is space for parking three cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

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Select Dates for Price

Private Vacation Home

Forest Hollow | Waterfront • Kayaks • Wood Stove

Monterey, Massachusetts, United States

Take a step out of everyday life and enjoy some rest and relaxation at this cozy home on the lake nestled in the hills of The Berkshires.brbrLay out on the docks, swim in the water, enjoy the foliage and unwind by the fireplace after a day of skiing! This place really has all the comforts anyone may need after a day spent enjoying the outdoors in The Berkshires.brbrCome see for yourself!brbr✔ Private lake access with dockbr✔ Cozy fireplacebr✔ Fully equipped kitchenbr✔ High-speed Wi‑Fibr✔ Coffee & essentials providedbr✔ Free parkingbr✔ Pet-friendlybr✔ Bathroom Essentialsbr✔ Outdoor Grillbr✔ Pack n Play Travel Crib (Upon request)brbr➥ 5 mins to Lake Garfield town beachbr➥ 12 mins to Butternut Ski Areabr➥ 19 mins to Beartown State Forestbr➥ 18 mins to The Mahaiwebr➥ 26 mins to Norman Rockwell Museumbr➥ 28 mins to Tanglewoodbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 1.5 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 QueenbrBedroom 2 - 1 Double bedbrBedroom 3 - 2 Single bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified. brbrThere is space for parking two cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

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$320.58

/ Nightly

Chalet

Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach

Monterey, Massachusetts, United States

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob s Pillow, Tanglewood.brbrThe SpacebrbrOur place is a beautiful rustic house in the woods with quiet privacy, the modern amenities you need to feel at home, and a view you will talk about after your visit ends. Easy access to Lake Garfield (lake access included), 10 Minutes from Ski Butternut, 15 minutes from Great Barrington.brbrThe main first floor living area is a lovely open space with galley kitchen, woodstove, ample seating for dining and relaxing. Sliding doors lead to the deck with lounge chairs and grill. Two bedrooms and a bathroom with tub round out the main level.brbrUpstairs you have a master suite: a lovely tucked away loft with proper closing door, king bed, tv, and en suite bath with shower.brbrDownstairs is a finished lower level with two twin beds, a queen sleeper sofa, den area w tv/video games, piano, laundry area, and doors that open to the outside under the deck. This is a flexible area, perfect for kids, well-appointed for adults.brbrGuest AccessbrbrOur house is a conveniently situated location from which to visit countless Berkshires attractions, including Tanglewood, Jacob s Pillow, Norman Rockwell Museum, W.E.B. Dubois National Historic Site, The Bidwell House Museum, Animagic Museum of Animation, Bard College at Simon s Rock, Berkshire Theater Festival, Berkshire Int l Film Festival, hiking at Umpachene Falls and Beartown State Forest, and a bit over an hour drive from MassMOCA. The charming towns of Great Barrington, Lenox and Stockbridge are all 15-20 minutes away. Lake Garfield Beach is a 20-minute walk or 4-minute drive down the hill. Ski Butternut, a hub for Northeast skiers, is a 10-minute drive, and a major attraction for winter travelers.brbrInteraction with GuestsbrbrThe house is yours and you will not be disturbed by us. Should you need anything we are always available over phone/text/email, and we have reliable local help, should problems arise.brbrOther things to note:brbr--The kitchen/main living space is only accessed by stairs, so keep that in mind for those with additional accessibility needs.brbr--The driveway is quite twisty! We recommend, minimally, a front wheel drive vehicle for winter stays.brbr--Parents with small children should be advised that any playing on the deck or at the foot of the deck/front side of the house must be monitored for safety, as there are spaces for a wee one to sneak thru the deck railing, and as there is a steep drop off into woods in front of the house.brbr—We aim to allow people to feel as comfortable here as possible, always are trying to improve guests’ experiences, and are almost always reachable and quickly responsive to any issues that arise. While we are here to help, guests should know it is not a hotel, but a lovely, rustic house in the woods. There are quirks; our patio door leaves a small crack which does not create any noticeable draft but does not seal tight. Some light switches were installed in strange places. We are as diligent as possible in the battle vs critters, as the woods is their home too, but there will occasionally be signs of a country mouse. It is on the side of a small mountain and there are storms that take the power out a few times a year. Workers can be hard to get here quickly. This is just life up here in the Berkshires, and we want guests to come with appropriate expectations so everyone is happy.br

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$544.54

/ Nightly

Private Vacation Home

Lake Haven with new dock and amazing views of Lake Garfield

Monterey, Massachusetts, United States

Relax with the whole family at this peaceful lakeside home. Enjoy the lake-facing deck for dining and drinks. Swim/boat/canoe/kayak/SUPB in Lake Garfield from our dock and enjoy the sun deck. View wildlife: bald eagles soar by, deer wander the woods, and many waterfowl and other birds. Prepare family meals from our fully appointed kitchen or enjoy dozens of nearby restaurants. We are close to Tanglewood, Great Barrington, Lee, Stockbridge & Lenox. Unwind in the Berkshires. We are dog friendly

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$1136.98

/ Nightly

Private Vacation Home

Monterey Home w/ Hot Tub, Pool & Game Room!

Monterey, Massachusetts, United States

Gather up your friends and family for the ultimate group getaway at this Monterey vacation rental! The home has nearly 4,500 square feet of interior space — including a game room, a huge sunroom, 6 bedrooms, 4 full baths, and 2 half baths — and plenty of outdoor space for everyone to enjoy. Plus, you’ll have easy access to endless outdoor adventures. Hit the slopes at Butternut Ski Area or Otis Ridge — both less than 10 miles away — take a hike on the local trails, or catch a show at Tanglewood!brbr-- THE PROPERTY --brbrMassTaxConnect ID C0463041930 | Deck w/ Gas Grill | Furnished Sunroom | 8 Mi to Butternut Ski Area | 15 Mi to TanglewoodbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: Queen Bed | Office: Queen Sleeper Sofa | Basement Bonus Room: Queen Bed, 2 Twin Sleeper Chairs | Additional Sleeping: Full Air Mattress brbrINDOOR LIVING: 3 Smart TVs, fireplace (wood provided), ping-pong/pool table, arcade machine, foosball table, board games, home officebrOUTDOOR LIVING: Pool (depth 4’-9’), hot tub, large backyard, playset, basketball hoop, pickleball netbrKITCHEN: Dishwasher, 6-burner gas stovetop, oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig K-Duo, percolator, coffee provided, toaster oven, beverage fridge, trash bags & paper towelsbrGENERAL: Free WiFi, central A/C & heating, complimentary toiletries, linens & towels, in-home laundry, laundry detergent, hangers, hair dryer, keyless entry brFAQ: 3 exterior security cameras (facing out)brACCESSIBILITY: 4 steps for entry, 3-story home, bedroom & full bathroom on 1st floorbrPARKING: Garage (2 vehicles), driveway (4 vehicles)brbr-- THE LOCATION --brbrSKI RESORTS: Butternut Ski Area and Tubing Center (8 miles), Otis Ridge (9 miles), Bousquet Mountain Ski Area (19 miles), Catamount Mountain Resort (19 miles), Ski Sundown (33 miles)brOUTDOOR ADVENTURES: Lake Garfield Beach (2 miles), Diane's Trail Trailhead (3 miles), Otis State Forest (8 miles), Tolland State Forest (16 miles)brEXPLORE THE AREA: Berkshire Botanical Garden (13 miles), Tanglewood (15 miles), Berkshire Museum (20 miles)brAIRPORTS: Bradley International Airport (43 miles), Albany International Airport (62 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 3-story home requires 4 steps for entry. While there is a bedroom and a full bathroom on the 1st floor, additional stairs are required to access bedrooms on the 2nd floor and in the basementbr- NOTE: Your safety matters. This property features 3 exterior security cameras: camera 1 is on the front patio facing the driveway, camera 2 is above the garage facing the driveway, and camera 3 is on the back of the house facing the yard/pool. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound

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$367.3

/ Nightly

Private Vacation Home

Stunning Renovated Home w/ Wood Burning Stove & Hot Tub !

Monterey, Massachusetts, United States

Looking for comfort and style! This fully renovated 3BR Monterey, MA home features an open floor plan, wood-burning stove, private hot tub, and is just minutes from charming towns, shopping, theater, winter fun and top Berkshires ski mountains. Family-friendly, cozy, and perfect for quality time. Ideal for a family looking to enjoy everything the Berkshires has to offer!brbrThe best of both worlds - outdoor lovers will enjoy access to hiking trails, snowshoeing, and scenic winter landscapes right outside your door OR explore a multitude of charming towns, local shops, farm-to-table restaurants, world-class theater, dance, and many live music venues just a short drive away. Whether you're here for adventure or relaxation, the Berkshires offer something for everyone.brbrSpacious, Serene 3-Level Home – Sleeps Up to 8 GuestsbrThis peaceful, fully renovated home offers comfort and flexibility across three levels—ideal for families or small groups looking for a cozy winter-season getaway.brbrMain Level:brBright and airy with vaulted ceilings, skylights, and an open-concept great room featuring a classic wood-burning stove—perfect for warming up after the slopes. The chef’s kitchen is fully equipped and boasts an oversized island, ideal for family meals and entertaining. Step outside onto the wraparound deck to take in seasonal lake views, enjoy the gas grill, or dine under the stars. This level also features a primary suite with ensuite bath for added comfort and privacy.brbrUpper Level:brA spacious loft offers a cozy nook for reading or playtime. This floor includes a second primary bedroom and a charming bunk room, both sharing a full bath—perfect for kids or additional guests.brbrLower Level:brA private walk-out den doubles as a TV room and workout space, with a queen pull-out sofa for extra sleeping options. Enjoy direct access to the hot tub and patio, your go-to spot to relax and recharge after a day of skiing or exploring the Berkshires.brbrWinter Season Highlights:br* Private hot tub – perfect for relaxing après-skibr* Wood-burning stove + fire pit for cozy winter nightsbr* 1-car garage – easy access during snowstormsbr* Gas grill available year-round (yes, even in winter!)br* Full access to all 3 levels – ideal for families or groupsbr* Quiet, walkable neighborhood – peaceful & family-friendlybr* Fully renovated with open-concept layout – warm, modern, and invitingbr* Minutes from top Berkshires ski resortsbr* Perfect for full-season stays – unpack and settle in!

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$406.0

/ Nightly

Private Vacation Home

Hupi Hills | town beach • Kayaks • shared court`s

Monterey, Massachusetts, United States

This house is located in peaceful Monterey less than a miles walk from the lake. Relax and unwind on the lovely grounds, cook up some food for friends out on the back patio, or take a short drive down to the town beach where a couple of kayaks will be waiting for you. After your paddle, rinse off in the outdoor shower and finish the night off outside by the fire. Doesn`t get much better than this home nestled right into the lakeside community that is Monterey.brbr✔ High-speed Wi-Fi (1 gbps)br✔ TVbr✔ Full kitchenbr✔ Washer & dryerbr✔ Free parkingbr✔ Shared tennis and pickleball courtbr✔ Large private grass yardbr✔ Outdoor firepitbr✔ Kayaks br✔ Pack n Play Travel Crib (Upon request)brbr➥ 3 min to Lake Garfield Beachbr➥ 8 mins to Beartown State Forestbr➥ 13 mins to Ski Butternutbr➥ 18 mins to The Mahaiwebr➥ 20 mins to The Berkshire Theatrebr➥ 20 mins to The Lion`s Denbr➥ 21 mins to W.E.B. Du Bois National Historic Sitebr➥ 27 mins to Norman Rockwell Museumbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 2 Twin bedsbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified. brbrThere is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months. brbrPlease note that clay tennis court directly on the property is not available for guests. There is a shared tennis court two lots down for guests to use.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

3

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3

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6

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