Vacation Rentals By Owner In Stockbridge, MA

The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from the Mass Pike it is an easy commute from Boston or New York City. brbrThe house has 8 foot ceilings and provide a nice 'vacation' like feel with every bedroom but one having its own bath. The common areas are designed for fun and socializing with family and friends.brbrThe 6 fireplaces provide ambiance and a feeling of escape into a time long forgotten. Play a game of pool, chess or checkers with your family. Enjoy two kitchens in which to work from, sit together at the 12 person dining area while enjoy a fire in the large hearth as you drink your wine and soak in the feeling of the Berkshires. brbrThis home has it all and it is designed to give you and your group a relaxing and fulfilling vacation.brbrKeywords: The Williams House dates to 1797 and has been completely updated in 2010. This home boasts 6 bedrooms, 5.5 baths, two terraces, 6 fireplaces, two full service cook's kitchens, a billiard room, large family room, dining area and table that seats 12 and a lounge/game area. This is the ultimate vacation rental. The house is situated 2 miles from Stockbridge Center, on 4 acres of pristine land with two patios and large grassy areas for outdoor fun. Enjoy all that the Berkshires offer while staying in luxury with your family and friends.

General Williams Estate House Lenox/Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$808.73

Absolutely stunning 2018 build less than 1 mile from downtown Stockbridge and an 8 minute drive to Ski Butternut and downtown Great Barrington. This 3 bedroom 3.5 bath is tucked away on a private road with one acre of peace and quiet. The grounds are immaculately maintained with a sitting area surrounding a Solostove firepit and a 6 person hot tub on the private back patio.brEnter on the main level to experience 11ft ceilings spanning the light filled open floor plan. Main floor features the dining area, which seats up to 6-8 people, modern kitchen, and the living room with floor to ceiling stone remote controlled fireplace and a 50 smart TV. This floor also features the primary bedroom with a private bathroom and a large walk in closet. Enjoy the furnished deck off the dining area and utilize the laundry room past the kitchen, as well as the half bath and ample closet storage.brLower level features a large bedroom with a private bathroom, and another bedroom with a full bathroom. Unwind and hangout in the lower den area with a wrap around couch, a 65 smart TV, and ample books and games. Walkout to the hot tub and firepit.brRelax with the quiet woods and peaceful interior, stay connected and entertained with high speed internet and smart televisions, and explore the trails, lakes, mountains, arts and country life of the Berkshires.

Spacious & Modern Berkshires Getaway

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$1038.81

Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Perfect for families, groups, or anyone seeking a serene escape, this charming property combines timeless elegance with modern amenities for an unforgettable stay.brbrEnjoy spacious, beautifully designed rooms that accommodate 8-12 guests, ideal for gatherings or peaceful retreats. Relax in the tranquil garden or explore local landmarks, including the nearby Divine Mercy Shrine, a haven for reflection and spiritual renewal.brWhether you're planning a weekend escape, a family reunion, or a quiet retreat, this one-of-a-kind Stockbridge gem offers comfort, history, and a truly divine experience. Book your stay today and immerse yourself in the beauty of the Berkshires!br

Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$1373.91

Stunning 5BR/5.5BA 4,500 sq ft home with soaring 25-ft ceilings, modern finishes, pearched in the trees with sparkeling views of the Housatonic River. This sun-drenched retreat features an open floor plan, chef’s kitchen, and floor-to-ceiling windows. Walk down wide, lit up, sidewalks just a block from downtown Stockbridge and The Red Lion Inn, and 2 miles from Tanglewood, the Norman Rockwell Museum, Chesterwood, and the Berkshire Botanical Garden. Ski Butternut & Bousquet (6 mi), Catamount & Jiminy Peak (12 mi). Explore the best of the Berkshires, right at your doorstep. Perfect for families, groups, or a luxurious getaway.

Country House

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge, Massachusetts, United States

5

Bed

5

Bath

10

Sleeps

$387.56

Welcome to your Berkshires getaway in the heart of Stockbridge. This charming, sun-filled home offers 3 comfortable bedrooms and 2.5 baths, perfect for relaxing with family or friends. Gather in the inviting living room, cook and linger over meals in the bright kitchen and dining area, then unwind outdoors in the spacious yard and patio. Just minutes from the Norman Rockwell Museum, Tanglewood, scenic hikes, and local shops and restaurants—this is an ideal home for exploring and slowing down.brbr✔ High-speed Wi-Fibr✔ TVbr✔ Fully-equipped kitchenbr✔ Spacious yard and patiobr✔ Washer & dryerbr✔ Free parkingbr✔ Outdoor grillbr✔ Air conditioningbr✔ Heatingbr✔ Pack n Play Travel Crib (Upon request)brbr➥ 2 mins to Berkshire Botanical Gardenbr➥ 3 min to The Lion`s Denbr➥ 5 mins to The Unicorn Theatre: Berkshire Theatre Groupbr➥ 5 mins to Norman Rockwell Museumbr➥ 5 mins to Chesterwoodbr➥ 7 mins to Stockbridge Bowlbr➥ 8 mins to Tanglewoodbr➥ 9 mins to The Mount, Edith Wharton`s Homebr➥ 10 mins to Olivia`s Overlook at Yokun Ridge Reservebr➥ 11 mins to Shakespeare & Companybr➥ 13 mins to Laurel Lakebr➥ 13 mins to Ski Butternutbr➥ 14 mins to The Mahaiwebr➥ 17 mins to W.E.B. Du Bois National Historic Sitebr➥ 18 mins to Bousquet Mountain Ski Areabrbr✦BEDS & BATHS✦brInside we have 2 bedrooms (plus office space with fold out sofa) and 2.5 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bedbrOffice / Bedroom 3 - 1 fold out sofabrbrAll 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.brbrThere is space for parking one car in the garage. Additional parking for multiple cars available in the driveway.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.

Hearth House | Prime Location!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$224.44

Spend the SUMMER in the HEART of the BERKSHIRES! JUST minutes from both the Lenox and Stockbridge Town Beach with access to both! 7 minutes from Tanglewood. Experience the MAGIC of Summer in the Berks in this tastefully decorated, fully furnished, and spacious 3 Bedroom & 3 FULL Bath Condo with balcony overlooking the pond. Fully equipped kitchen and smart TV. Just minutes to Stockbridge, Lenox, and Lee! 4 week MINIMUM. Discount available for long term stay! This condo is also available for ski season and the Spring, Set up a time and come for a tour. You will love it!! Check out this video and follow us on insta: @serenelifeberkshires! https://youtube.com/shorts/eHKEvV9MtY8 si=M4XCR6Q3_3Za4EBhbr

Condo

Summer in the Berkshires!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$393.18

My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - great views, the city center, art and culture. You’ll love my place because the view from our home looks down upon the Housatonic river, and the oldest preserve in Massachusetts - the neighborhood, the ambiance, the comfy beds, the light, the outdoors space. My place is good for couples, solo adventurers, business travelers, and families (with kids). The place is newly renovated.

Two Blocks from the Red Lion Inn & next to Berkshire Theater

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$692.37

Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires.brbrThis sleek, contemporary escape will take your breath away from the moment you arrive. Surrounded by lush greenery, its modern exterior is a unique contrast with the natural landscape. Step onto your spacious deck, complete with comfortable seating and a BBQ grill, and immerse yourself in the serenity of the surrounding woodland.brbrFloor-to-ceiling windows flood the living spaces with natural light, offering stunning views of the picturesque landscape. The bright, open living room features a large fireplace, plush seating, and a TV. Need more space Discover a second sitting area with an additional sofa and TV.brbrEntertain in style in the sleek dining area, nestled next to the windows and overlooking the patio. With seating for 8, it's perfect for gatherings. Plus, there's another dining table in the adjacent sunroom with seating for 6.brbrCooking is a breeze in the fully equipped kitchen, boasting stainless steel appliances, a gas range, and ample counter space. Additional barstool seating ensures everyone has a place to gather.brbrRetreat to one of three comfortable bedrooms, each featuring a plush queen bed. The primary suite boasts an attached ensuite bathroom and access to the patio, perfect for enjoying your morning coffee in peace.brbrConveniently located just 10 minutes from Great Barrington, you'll have easy access to dining, shopping, wine tasting, and outdoor adventures.brbrWith in-home laundry and parking, Woodland Zen offers the ultimate blend of luxury, privacy, and convenience for your Berkshire getaway.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 ResortbrbrHome Truths:br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval, there is a fine of $500 per pet.brbrParking Details:br- Parking is available onsite for 4 vehicles in the carport and driveway.br- No street parking is permitted.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed w/ ensuitebrBedroom 2 / Queen bed brBedroom 3 / Queen bed brbr---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 28 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

Stockbridge, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$366.23

This stylish newly renovated 2 bedroom apartment is walking distance to downtown Stockbridge. It is the main floor of a two story structure, the space boasts a relaxing front porch and a private back deck. The open living space is comfortable and modern. There is a spa like bathroom with a tiled steam shower. A fully equipped kitchen with new appliances and full size laundry. The bedrooms are spacious, one with king bed and the other with a queen. Full size laundry machines and a gas fireplace on the rear deck.

Stockbridge In-town Escape

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$317.23

Refurbished cottage, perfect for a couples getaway. This retreat is tastefully decorated with with local antiques & fresh linens. Nestled into the forest in the best possible location, just one mile from Tanglewood and an 5 minute walk to Stockbridge Beach. Lots of places to put your feet up with a good book, or just enjoy the sound of the wind in the trees. This is a seasonal camp with a/c in the bedrooms. You can also expect an occasionally visit by a local bear, chipmunk or red wing hawk.brbrWe encourage our guests to follow local orders regarding COVID. Information can be found on the Town of Stockbridge website. Feel free to ask what we do to keep the cottage clean for you.

Cabin

Artist's Camp on Lake Mahkeenac

Stockbridge, Massachusetts, United States

2

Bed

Bath

4

Sleeps

$335.1

Get ready to relax in this 4-bedroom cottage in the Berkshires in Stockbridge, MA. The space features four cozy twin beds and one full bed, perfect for families or groups. With two an 1/2 bathrooms that include refreshing showers, guests enjoy plenty of privacy and convenience. The cottage stays comfortable in the Spring, Summer and Fall. There is heating throughout and a portable AC in the master bedroom and fans in every room. Step inside to find a cool, inviting atmosphere where you can unwind after a day of exploring. This wonderful retreat offers a peaceful escape that guests will love. Make your holiday one for the books with a stay at our place. We are a 10 minute walk to a private beach (where you can have use of our kayaks) on the Stockbridge Bowl and only a 10 minute drive to Tanglewood.

4-bedroom cottage in Stockbridge MA in Berkshires, minutes to private beach

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$376.86

Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private deck, fireplace, in-unit laundry, and 114 acres of property to explore, this home-away-from-home can’t be beat! When you aren’t enjoying the stunning exterior space on the expansive deck or spotting wildlife like owls, foxes, and deer, venture off-site for skiing at Butternut Basin or swimming at Stockbridge Bowl. Whether snowy or sunny, endless adventures await!brbr-- THE PROPERTY --brbr1,600 Sq Ft | Pets Welcome | Free WiFibrbrNestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat, complete with tranquil privacy and modern comforts. brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds brbrOUTDOOR LIVING: Gas grill, 114 acres of hiking trailsbrKITCHEN: Fully equipped, drip coffee maker, Keurig coffee maker, toaster, electric pancake skillet, ice cube maker, cafe tablebrINDOOR LIVING: 2 TVs, HD TV, fireplace, dining table, Apple Mac-Mini computer, cell phone charging stationbrGENERAL: Washer & dryer, towels, linens, complimentary toiletries, central air conditioning/heat, keyless entry, pet fee (paid pre-trip)brSUITABILITY: Stairs requiredbrPARKING: Driveway (2 vehicles), detached garage (1 vehicle), outdoor area (1 vehicle)brbr-- THE LOCATION --brbrSTOCKBRIDGE BOWL (4.0 miles): Stockbridge Town Beach, BSO Beach, Stockbridge Bowl Boat Ramp, boating, swimming, fishing, kayaking, paddle boarding, canoeingbrHIKING: 114 acres on-site, Stevens Glen Trail Head (4.8 miles), Monument Mountain Reservation (4.8 miles), Olivia's Overlook (5.5 miles), Brothers Trail (6.0 miles), Burbank Trail (6.2 miles), Parsons Marsh Reserve (6.5 miles), Appalachian Trail (12.1 miles)brLOCAL ATTRACTIONS: Norman Rockwell Museum (1.4 miles), Orleton Farm (3.7 miles), Tanglewood (5.6 miles), Koussevitzky Music Shed (5.8 miles), Seiji Ozawa Hall (6.7 miles), Frelinghuysen Morris House & Studio (6.7 miles), The Playhouse (6.9 miles), Ventfort Hall Mansion and Gilded Age (7.4 miles), The Mount, Edith Wharton's Home (7.5 miles)brSKIING: Ski Butternut (9.9 miles), Catamount Mountain Resort (14.6 miles), Jiminy Peak Mountain Resort (25.8 miles)brAIRPORT: Albany International Airport (48.0 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- Massachusetts Tax ID: C0214960870br- No smokingbr- Pet friendly w/ $75 fee (+ fees & taxes, maximum 3 pets allowed)br- No events, parties, or gatherings of more than 6 peoplebr- No fireworks allowed on the propertybr- Garage is unavailable during winter months (11/15-4/15)br- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Access to the home requires stairs

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge, Massachusetts, United States

Bed

Bath

6

Sleeps

$524.94

Located in Stockbridge, this marvelous home away from home offers a comfortable retreat for the whole family! With three bedrooms featuring one queen bed and four twin beds, there’s plenty of space for family or friends. The three bathrooms include showers and a tub along with handy hair dryers and all basic essentials to make mornings easy. Enjoy a beautiful environment located down a private road, acres of beautiful yard space and a beautiful deck to enjoy coffee or dinning outdoors! Whether you’re gathering in the cozy living areas or unwinding after a day of exploring, this terrific home provides a welcoming atmosphere. Kick back, relax, and enjoy everything Stockbridge and our house has to offer.

Light Filled Modern Rustic 3-bedroom house in charming Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

6

Sleeps

$351.43

Escape to this charming cottage in picturesque Stockbridge. Guests will enjoy a serene retreat featuring one cozy bedroom with a king bed and a clean, modern bathroom with a refreshing shower. The space stays comfortable with air conditioning, and an iron is available for any quick touch-ups. Whether you’re unwinding after a day of exploring or simply soaking in the peaceful surroundings, this excellent cottage offers a marvelous spot to relax. Our place will help you feel at home while you're traveling in Stockbridge.

Light-filled Carpenter's Cottage

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$283.91

Our darling cottage is a lovely, quiet retreat just minutes from some of the most iconic spots in the Berkshires! brbrThe Norman Rockwell Museum and Berkshire Botanical Gardens are within walking distance. Chesterwood Museum and Boston Symphony's summer home at Tanglewood are just down the road, along with Herman Melville's Arrowhead, Edith Wharton's The Mount, Ski Butternut and many other local attractions. Fewer than five minutes from Stockbridge's historic main street made famous by Rockwell, this cottage provides the perfect home base for a relaxing and memorable stay exploring all that Western Massachusetts has to offer. brbrThe upstairs king bedroom suite boasts a pastoral view of the spacious grounds and forest beyond. Enjoy a generous living/dining space and relax on the adjoining patio overlooking the groomed lawn and gardens. Kitchenette is equipped with countertop convection oven, coffee pot, four-burner cooktop, and mini-fridge. Upstairs also accommodates a double trundle (two twin beds) for couples with small children. Garage bay available with remote for convenient parking, loading/unloading during inclement weather.brbr ***Ask about our off-season rental option!! ***br***Special monthly rates Nov 2025 through April 2026 ***brbrPerfect for the remote worker who would love to escape the city for beautiful Berkshire living in the wintertime. Bring your laptop, books, winter clothes, and skis and prepare to snuggle in for a beautiful season in one of the most idyllic spots in western Massachusetts.

Fabulous Tanglewood Getaway!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$282.78

Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake activities, Tanglewood, the Norman Rockwell Museum, and hiking trails - all found within a short drive. Ease into your mornings with a good book and a steamy cup of coffee on the private porch, and later, walk to the lake for a picnic!brbr-- THE PROPERTY --brbrC0077602830 | Free WiFi | Expansive Deck | SunroombrbrIndulge in a leisurely Berkshires lifestyle when you stay at this cozy, light-filled cabin. Ideal for pairs of two looking to escape modern distractions and spend time in nature.brbrBedroom 1: King Bed | Bedroom 2: 2 Twin Beds (Photos Coming Soon) | Sunroom (Not Private): Twin Bed w/ Twin Trundle BedbrbrOUTDOOR LIVING: Large deck w/ outdoor dining table, lounge chairs, gas grill, 2 kayaks, 2 stand up paddleboards, beach chairs, outdoor shower, walk to lakeshore, neighbors nearby (please be respectful of the noise level outside)brINDOOR LIVING: Vaulted ceilings, open layout, high-top counter seating, desk, ample natural light, bright interior, flat-screen Smart TV (no cable), 2 cozy bedrooms, 2 full baths, 800 square feet totalbrKITCHEN: Well equipped, dishwasher, gas range stove, toaster oven, microwave, drip coffee maker, cooking basics, dishware, flatware, pots, pansbrGENERAL: Linens/towels, window air conditioning, first aid kit, Pack 'n Play, washer/dryer, wall heaters, space heaters, ceiling fansbrPARKING: Driveway (3 vehicles max)brbrThis charming seasonal cottage dates back to the 1940s. It still maintains much of its original details and rustic charm, which is balanced nicely by its freshly whitewashed interior, comfortable amenities, welcoming decor, and brand new cedar outdoor shower.brbrThoughtful touches like picnic blankets, beach towels, and even a record player and albums make this cute cabin an easy place to call home during your Berkshire vacation.brbrSituated at the edge of the woods on a shared, dead-end drive, the cottage offers the perfect place to get away (and possibly even see some wildlife!) while being just minutes from Lenox and Stockbridge and walking distance to the lake beach. And, when the wind is just right, you can even hear the faint sounds of Tanglewood's music drifting across the lake on a warm summer night.brbrNote from the owner: We have so many happy memories at 'Elandee,' named after our two daughters, L and E. We hope that if you choose to stay, you have an enjoyable and memorable time here, too!brbr-- THE LOCATION --brbrSTOCKBRIDGE BOWL: Stockbridge Town Beach (0.1 miles - 5-min. walk), BSO Beach (2.3 miles), Stockbridge Bowl Boat Ramp (3.1 miles), boating, swimming, fishing, kayaking, paddle boarding, canoeingbrHIKING: Brothers Trail (3.2 miles), Parsons Marsh Reserve (3.4 miles), Olivia's Overlook (3.8 miles), Burbank Trail (3.8 miles), Stevens Glen Trail Head (4.5 miles), Monument Mountian Reservation (6.2 miles), Appalachian Trail (11.6 miles)brLOCAL ATTRACTIONS: Orleton Farm (0.9 miles), Koussevitzky Music Shed (1.9 miles), Seiji Ozawa Hall (2.0 miles), Frelinghuysen Morris House & Studio (2.0 miles), Tanglewood (2.5 miles), Ventfort Hall Mansion and Gilded Age (3.4 miles), Norman Rockwell Museum (3.8 miles), The Mount, Edith Wharton's Home (4.4 miles), Cranwell Mansion (4.7 miles), The Playhouse (5.5 miles)brSKIING: Ski Butternut (11.3 miles), Catamount Mountain Resort (18.0 miles), Jiminy Peak Mountain Resort (25.4 miles)brAIRPORT: Albany International Airport (51.5 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 property is best suited for 4 guests, but can sleep a total of 6 with the use of the non-private sunroombr- NOTE: This property is not suitable for children under 12br- NOTE: Your safety matters. This property features 2 exterior security cameras, above the front door and the deck, all facing outward. They do not look into interior spaces

Cabin

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$454.0

4 bedrooms, sleeps 7, 2 living rooms, 2 full bathrooms, fully stocked kitchen; lawn chairs, beach towels, games, and bicycles to use.brbrWe are happy you are interested in our beloved cottage!brbrThis lake house is not your typical vacation rental. This really is Grandma and Grandpa’s country home away from home for 55 years, and they love having all their old stuff full of memories still there. They are a simple couple that grew up in hard times, now 95! So they don’t buy new things often, and are comfortable with stained beach towels. We focus on the experience and time together rather than material things. brbrSo with that being said we have not replaced the bedding, rugs, or TV. Everything is throughly cleaned and disinfected, even fresh paint!; but it is all still old stuff, that still works!brbrThere is no A/C, but there are plenty of windows and each room has at least one fan in it. There is heat. brbrThere is plenty of space for your belongings when you check in. At least the top 2 drawers in all rooms are clean and empty. Each bed has its own light and outlet close enough to not get up from the multiple pillows provided.brbrThe other thing you should know is that the water is high in iron and always has been, and since the cottage is closed up for the winter you will see rust in toilets and sinks slightly. I assure you it is fine to shower and wash dishes and clothes, but please do bring drinking water. brbrEven though it’s an old county cottage it is a 2 min walk to the beautiful lake in a safe, private and friendly community with plenty of room for the whole family, a huge yard and many amenities to help you enjoy your vacation; like bikes, balls, lake toys, board games, full working and stocked kitchen, and a working Apple TV on our old school TV!brbrPlease let us know if you have any questions.

Grandparent’s Cottage 250 steps to the lake

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$557.06

Welcome to Beaver Creek by AvantStay!brbrTucked amid the rolling hills and vibrant forests of Stockbridge, Beaver Creek is a storybook escape where New England charm meets modern comfort. This picturesque retreat sits surrounded by lush gardens and autumn-kissed scenery, offering a front-row seat to the Berkshires’ beauty—just minutes from the serene Stockbridge Bowl, historic Main Street, and cultural icons like Tanglewood and the Norman Rockwell Museum.brbrStep inside to discover bright, inviting interiors that balance timeless elegance with relaxed comfort. The living room, wrapped in soft whites and natural light, centers around a cozy wood-burning fireplace—perfect for gathering after a day exploring nearby trails or art galleries. Adjacent, the dining room seats eight for memorable meals, while the fully equipped kitchen makes entertaining easy with its modern finishes and sunny window views.brbrFour serene bedrooms promise peaceful rest, including two spacious king suites and a cheerful bunk room ideal for kids or friends. The primary suite offers a spa-like ensuite bath with a soaking tub and walk-in shower, while an additional full bathroom and half bath ensure comfort for all.brbrOutdoors, you’ll find every reason to linger—from morning coffee on the covered porch to sunset barbecues in the crisp mountain air. The patio features a grill, picnic table, and lounge seating for six, surrounded by manicured landscaping and views that shift beautifully with the seasons.brbrWhether you’re leaf-peeping in the fall, skiing at nearby resorts in the winter, or soaking in lake breezes come summer, Beaver Creek invites you to experience the best of the Berkshires in style and serenity.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. brbrVisiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else.brbrLocal Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort. Visit High Lawn Farm, a beloved local creamery known for its farm-fresh ice cream, handcrafted cheeses, and artisanal dairy made right in the Berkshires.brbrHome Truths:br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- The property uses well water, which is safe for consumption and daily use.br- The home operates on a septic system, so please avoid flushing anything other than toilet paper.br- A static lock code provides access to both the main gate and the house.br- Firewood is not provided; please bring your own if you plan to use the fireplace or fire pit.br- This home is located on a working farm, so guests may notice occasional farm activity such as tractors, planting, and harvesting.br- Local wildlife may be present in the area, so please enjoy with care and keep food securely stored.br- A pack ’n play and high chair are available for guest use.brbrParking Details:br- Parking is available in the driveway for up to 6 vehicles; the garage is not accessible, but there are no neighborhood parking restrictions.brbrAll bookings over 30 days require a security deposit to be charged after booking.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 28 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$311.65

*Beyond the north side of the property lies the turnpike, so there is some road noise. We rarely notice it, especially inside the house, but we want to point this out to those who are sensitive to traffic noise.*brbrThis adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While it is a short distance away from our family home and one can hear the ambient hum of the highway, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck.brbrThe cottage sleeps 2 in the queen sleigh bed, but there is seating for a dinner party of 6. It sits on a south-facing hill, looking out towards Monument Mountain. You’ll love it!

Light-filled Carpenter's Cottage w/ EV charger!

Stockbridge, Massachusetts, United States

Bed