Vacation Rentals By Owner In Monterey, MA

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:

Beautiful Berkshire family home

Monterey, Massachusetts, United States

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Bath

Sleeps

Exceptional(99)

$603.18

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.

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

Monterey, Massachusetts, United States

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Bath

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Exceptional(11)

$1163.55

Imagine waking up to soft morning light streaming through skylights, brewing coffee in a designer kitchen, and stepping onto your deck to overlook the peaceful waters of Lake Garfield. Welcome to our newly renovated 5BR Berkshire lake & ski retreat—thoughtfully reimagined by an Architect and Interior Designer to create a serene, elevated vacation experience.brJust 5 minutes to Ski Butternut, 20 minutes to Catamount, and 15 minutes to vibrant downtown Great Barrington, you’ll be perfectly positioned to enjoy the best of the Berkshires: skiing, hiking, dining, shopping, and endless outdoor adventures.brInside, the home is bright, spacious, and designed for groups of 12–14 to relax in comfort. Enjoy 5 bedrooms, 4 full bathrooms, 2 living rooms with oversized smart TVs and wood burning fireplace, a fully equipped chef’s kitchen, dining room, and front & rear decks with BBQ.brNatural light fills the house, framing views of the lake and surrounding trees.brStep outside to enjoy a 6-person hot tub with lake views, a fully fenced backyard perfect for families and pets, and a Solo Stove smokeless fire pit sitting area for cozy evenings under the stars.brA short 5-minute walk brings you to the white-sand public beach of Lake Garfield, with picnic tables, lifeguards in season, floating docks for swimmers to use and a boat launch. Guests are welcome to use our 2 kayaks, conveniently stored by the beach during summer months.brWhether you’re planning a ski trip, summer lake vacation, family gathering, or relaxing Berkshires getaway, our home provides the perfect setting. From peaceful mornings by the water to evenings around the fire pit, every moment here feels like a true escape.brBook your unforgettable Berkshires stay—lakefront living, designer comfort, and incredible outdoor access await.

Sleek Butternut Ski Chalet Lakefront with Hot Tub & Sauna Near Great Barrington

Monterey, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$386.2

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.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.

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

Monterey, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$574.46

Welcome to our charming lakeside cottage on Brewer Pond, the tranquil extension of Lake Garfield, with a neighboring standalone barn/rec room! If you're seeking a serene getaway with an array of outdoor activities, this is the perfect spot for you.brbrWhether you're an adventure seeker, nature lover, or simply wish to unwind in a peaceful environment, our cottage has something special to offer for everyone.brbrStunning Lake Views: Start your day with breathtaking views of the shimmering waters right from the comfort of the cottage. Enjoy the stunning sunsets while sitting on the private deck or around the fire pit in the evenings.brbrWater Activities: Embrace the wonders of Brewer Pond with our provided kayaks & canoes. Paddle along the peaceful waters, explore the hidden coves, and immerse yourself in nature's beauty. Fishing enthusiasts will find the pond teeming with various species to catch. Make sure to say hi when paddling past the local beaver lodge!brbrBiking Adventures: Discover the surrounding area on two wheels. We have bicycles available for your use, making it easy to explore the nearby trails and scenic routes.brbrRec Room: For some indoor fun, head to the rec room equipped with board games, a dart board, and other entertainment options. It's an ideal spot for friendly competitions and family bonding.brbrCozy Living Area: After a day of exploration, unwind in the comfortable living area. Kick back on the plush sofas, watch your favorite shows on the flat-screen TV, or simply enjoy the company of loved ones. Feel free to enjoy the library of books at your convenience!brbrOutdoor Dining: Savor your meals in the great outdoors under our beautiful pergola, perfect for enjoying the fresh air and lovely lake views.brbrPet-Friendly: We understand that pets are part of the family too! Well-behaved furry friends are welcome to join your lakeside retreat.brbrNearby Attractions:brbrLake Garfield Beach: Enjoy a larger sandy beach area for swimming and sunbathing just a short distance away.brbrTanglewood: Experience live concerts & shows from the best that the Berkshires has to offer!brbrButternut: less than 10 minute drive away for the Berkshires favorite family ski mountainbrbrBerkshire Theater Festival: Enjoy Summerstock theater for all your summer playsbrbrJacob's Pillow: The go-to Berkshire spot for modern dance!

Cabin

Cozy Lakeside Cottage Oasis

Monterey, Massachusetts, United States

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Bath

Sleeps

$753.93

Laurel Banks Waterfront: Amenities include 4 bedrooms, 2 full baths, all new mattresses and linens, high-speed fiber optic internet, three (3!) Smart TVs with access to all subscriptions TV - please bring your logins - central AC, Sony turntable, high-end appliances, washer/dryer, propane fireplace, outdoor seating with propane grill, fire pit, and large outdoor dining table with oversized umbrella. Direct lake access off private dock with 2 new kayaks with life vests and water noodles and floats to enjoy. The lake permits small craft and speed boats/pontoon boats, etc. is perfect for swimming, boating, wildlife viewing, pretty sunsets, and fun winter sports (ice fishing, cross country skiing, snowshoeing, etc. - weather permitting).brbrWe love this cottage, which is available and perfect for enjoying every season! Enjoy all that the lake has to offer in summer, well into fall... or tuck into winter on Lake Buel and Ski Butternut, which is less than a 5 minute drive! Located in Monterey, MA (10 minutes away from the town of Great Barrington) this wonderful home has all the bells and whistles needed to be a great rental.brbrMAIN FLOOR has a an open floor plan with living, dining, and kitchen with sparkling views of Lake Buel. The living room has plenty of seating, with a new sofa, love seat, and oversized reading chair. Watch a movie on the brand new Samsung ”portrait” flat screen SmartTV that disguises itself as a piece of art when not in use! This space also has a new propane fireplace - so easy, with an on/off switch and a fun Sony turntable, with records supplied. The fully equipped kitchen has all high-end stainless appliances: dishwasher, fridge/freezer with ice maker, gas range, standard drip coffeemaker, microwave, toaster, slow cooker and many helpful gadgets. There are three (3) stools for the bar, looking into the kitchen, table seating for 4 or 6, snuggly. This area has such sparkling water views.... it is just beautiful. Three of the four bedrooms are located on the main floor, and these 3 bedrooms share a large full bathroom with a walk-in shower. The largest of the bedrooms on the main floor has a king size bed, dresser and SmartTV. Guest room #2 has 2 twins beds and guest room #3 has a queen size bed. This house is truly well equipped to keep families entertained with board games, puzzles, cornhole set, lawn darts and an impressive selection of newer fiction books to borrow.brbrThe SECOND FLOOR hosts the primary bedroom with a queen bed. This sunny bedroom has amazing views of the lake and it also has blinds for when you want to sleep in! This room has a large SmartTV, terrific walk-in closet, reading chair, and an ensuite bathroom with another large walk in shower.brbrThe LOWER LEVEL of the cottage has the washer/dryer, plus access to come and go outside through a small door and garage door that leads to the water. You'll find 2 kayaks, paddles, life vests and lake toys here and it's a great place ro store your outdoor gear as well. brbrOUTSIDE the kitchen is the large stone patio overlooking the lake with a large dining table with seating for 6, an oversized outdoor umbrella, and a propane fire pit with even more seating for guests to enjoy. Down, near the water, guests will find Adirondack chairs to sit and relax and take in the wonderful water views. The direct lake access permits small craft and speed boats/pontoon boats, etc. and there is are 2 kayaks with life vests included. The lake is perfect for swimming, boating, wildlife viewing, pretty sunsets and fun winter sports (ice fishing, cross country skiing, snowshoeing, etc) weather permitting. This cottage and this gorgeous lake does not disappoint! brbrLOCATION: Terrific year round location! Enjoy the lake during the summer and skiing in the winter with Ski Butternut only 5 minutes away, 10 minutes to Great Barrington, 15 mins to Stockbridge, and 25 mins to Tanglewood.brbrSee additional photos of the cottage and local attractions onthe gram at laurelbankslakehouse.brbrPlease inquire about Pets, which must be approved with a pet feebrNO SMOKING, Thank you!brbr***Please inquire about a local speed boat & jet ski rental company that can deliver the boat to the lake during your stay!***

Lake Buel Waterfront: with Sparkling Views, Fire Pit and Kayaks!

Monterey, Massachusetts, United States

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Bath

Sleeps

Exceptional(11)

$585.58

Summary:brFor your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham Valley. On the first floor, you will find a great room with vaulted ceilings and a fireplace, as well as a master suite, second bedroom, half bath and recently renovated kitchen. The second floor includes two more bedrooms and a bathroom. The exterior offers a screen porch with hot tub, wraparound deck and 35+ acres of woods bordering conservation land in Monterey.brbrThe Space:brnull.brbrGetting Around:brGuests will need a car in order to get to the property as well as to enjoy what the surrounding area has to offer. As the house is located on the side of a mountain, a car with four-wheel drive is recommended, and snow tires or chains are advised in icy weather.

Treetop Hideaway in Tyringham

Monterey, Massachusetts, United States

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Bath

Sleeps

Exceptional(29)

$511.96

Supremely relaxing modern home in wooded setting with screened in outdoor porch as well as a firepit, patio and gas grill. Close to public town beach. Close to Butternut, Catamount, Jimney peak as well as excellent hiking and biking. Great Barrington, Tanglewood, Jacobs pillow, great restaurants and markets close by.

Beautiful, peaceful modern home in a wooded area with town beach lake access

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(13)

$1691.41

Welcome to Forget-Me-Not by AvantStay!brbrBold, modern design perched right above the shores of Lake Garfield. Forget-Me-Not is a vast, three-story Berkshires retreat with unobstructed lake views, a lofted, industrial-chic design, and plenty of ways to keep your group comfortable and entertained. The home's moody exterior gives way to a bright, open common area where you'll find huge windows for tons of natural light, a spacious kitchen, and vaulted ceilings over the main living room. A cozy sunroom leads to Forget-Me-Not’s large deck, which features a BBQ grill and outdoor dining table for al fresco meals overlooking the water. Soak in the hot tub, or head inside for a round of ping pong, cornhole, or heat up in the custom-built sauna. The lower floor features a second living room complete with a kitchenette and pool table, so your group will have plenty of room to spread out. With tons of privacy and unbeatable proximity to the shoreline, this contemporary lake retreat is ready to show you the best of the Berkshires.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrA visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself!brbrLocal Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resortbrbr*Home Truths:*br- The dock is seasonal, it must come out of the water in fall & winter, like most docks on the lake, because the ice may permanently damage the docks.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- The driveway is paved and steep, making it suitable only for 4WD/AWD vehicles, particularly in winter months.br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.br- Guests must be 25 years or older to book this home.brbrParking Details:brDriveway space for 2 cars to park, and parking on the other side of the road, ~6 spots totalbrbrThis home comes with a pack n' play travel crib available. A high chair can be provided upon request with at least 24hrs advanced notice. Just ask and we are happy to accommodate you and your little ones!brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bedbrBedroom 2 / 2x bunk bedsbrBedroom 3 / King bedbrBedroom 4 / King bedbr+ 2 twin size tri-fold sleeping matsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.brbrTax #C1148950976

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

Monterey, Massachusetts, United States

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Bath

Sleeps

$243.86

This charming and appropriately named Little Cottage was newly renovated in 2017. Enjoy a short walk (300 feet) down a dirt road to a small beach and private dock on Lake Buel, beautifully situated in the heart of the Berkshires. brbrExperience new and contemporary furnishings in a country setting. Antiquing, rustic dining, skiing, hiking, theater and performing arts are only minutes away! Clay tennis courts on site. Great for families and outdoor enthusiasts or those that just want to unplug from it all.brbrThe cottage is just steps from the water where you can enjoy fishing, swimming, and boating on Lake Buel. There is a private community beach and dock. There is also a public boat ramp and parking lot just one street over. brbrThis Property is just a short walk from Camp Half Moon, a co-ed sleep-away summer camp for kids ages 6-16 that also offers half-day camps. brbrExperience all the Berkshires has to offer. brbr***Hiking / Orchards***brMonument Mountain (10 minute drive)brBeartown State Forest Park (10 minute drive)brBash Bish Falls (35 minute drive)brWindy Hill Orchards (10 minute drive)brHilltop Orchards (30 minute drive)brbr***Skiing / Adventure Parks (Summer)***brButternut Basin (7 minute drive)brJiminy Peak (1 hour drive)brCatamount (25 minute drive)brbr***Great Barrington (15 minute drive)***brdining, antiquing, bowling, movie theaterbrbr***Historic Stockbridge (15 minute drive)***brNorman Rockwell Museum, Berkshire Botanical Gardens, and Berkshire Scenic Railwaybrbr***The Arts***brTanglewood summer home of the Boston symphony orchestra (25 minute drive)brJacobs Pillow Dance (30 minute drive)brShakespeare and Company (25 minute drive)brBarrington Stage Company (20 minute drive)brMahaiwe Performing Arts Center (15 minute drive)brbr***Amenities***brWasher/dryer, dishwasher, microwave, coffee maker, gas stove/oven, electric heat and A/C, flatscreen TV with DVD player. UNPLUG AND ENJOY NATURE - There is no satellite or wi-fi and cell reception is spotty though AT&T providers work, most others do not.brbrbrBOOK EARLY TO GET THE DATES YOU WANT!!

Cabin

Steps to Lake Buel, close to Great Barrington & Stockbridge

Monterey, Massachusetts, United States

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Bath

Sleeps

Most popular vacation rentals in Monterey

$1270.59

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

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$312.19

Country House

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

Monterey, Massachusetts, United States

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Bath

Sleeps

$317.76

Cottage

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

Monterey, Massachusetts, United States

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Bath

Sleeps

$364.62

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey, Massachusetts, United States

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Sleeps

$488.29

Lake Haven with new dock and amazing views of Lake Garfield

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$511.96

Beautiful, peaceful modern home in a wooded area with town beach lake access

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$566.20

Fully Renovated / Peaceful Ski & Lake Retreat

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$574.46

Cabin

Cozy Lakeside Cottage Oasis

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$603.18

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

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$1163.55