House vacation rentals in Williamstown

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Top-rated house rentals in Williamstown

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Guest favorite

A two-story house is nestled in a snowy landscape, surrounded by bare trees. The exterior features a combination of beige and green, with large windows allowing for ample natural light. A covered deck with wooden beams and a patio area is visible in the foreground.

Home in Wilmington

5 out of 5 average rating, 10 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Enjoy stunning lake & mountain views w/ easy access to hiking, swimming, boating, & fishing (kayaks, paddle board, and bikes included). Cathedral ceilings w/ beams provide a cozy feel & heated floors give an always-warm home in the winter. Covered deck w/ grill is great for outdoor dining. Additional features include outdoor hot tub, sauna, & quality game room (pool table, shuffleboard, foosball, ping pong). 4WD/AWD required in winter. Close to Mt. Snow & downtown Wilmington w/ shops and dining.

Top guest favorite

The exterior of the lakefront home is displayed, featuring a two-story structure surrounded by greenery. A well-maintained lawn and rock garden enhance the inviting landscape. A shed is visible to the right, adding practical space to the property.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

The exterior of a red, two-story house is shown, featuring a gabled roof and a large, wraparound deck. The surrounding lawn is expansive and well-maintained, with greenery extending into the background under a bright blue sky with scattered clouds.

Home in Old Chatham

4.96 out of 5 average rating, 25 reviews

Post and Beam Hilltop Sanctuary

Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.

Top guest favorite

The exterior of the lakefront home showcases a vibrant blue facade, framed by well-maintained green lawns and leafy trees. A spacious deck is visible, along with multiple large windows that enhance the inviting appearance of the property.

Home in Valatie

5 out of 5 average rating, 112 reviews

Escape to Lakefront Leisure—Amazing views!

Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to maximize the incredible view of the lake. Cool and sunny in the summer, and warm and cozy in the winter. Come and relax on Lake Kinderhook!! Brand new 6 person hot tub. Relax and unwind while 45 jets massage your muscles, summer or winter! Ever sit in the steaming hot water while snow falls around you? Upgraded 400/100 internet for work/school! About 2 hrs from New York City!

Guest favorite

An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.

Home in Great Barrington

4.96 out of 5 average rating, 166 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Top guest favorite

The Batwing Ski House features a modern wood and stone exterior, characterized by large windows that invite natural light. A spacious lawn surrounds the home, with a classic red car parked nearby. A deck extends from the front of the house, offering outdoor accessibility.

Home in Dover

4.91 out of 5 average rating, 184 reviews

Mount Snow 5 Star Batwing House Spring Discounts

The Batwing Ski house was purchased and modernized with nice renovations The house was named the BatWing House over 20 years ago and still to this day everyone refers to it by name. It's a 6 bedroom 4 bath each with shower also a huge dining/ living area with corner fireplace. A ski/gear room on the first floor. New hot tub outside on the wrap around deck with covered roof. We have Fiber Wifi , Netflix, Xbox 360, foosball, board games 4 TVs. Restaurants are less than .5 miles away

Guest favorite

A serene forest pathway is covered in vibrant orange and yellow fallen leaves, framed by tall trees displaying autumn foliage. Sunlight filters through the branches, illuminating the scene and creating a warm glow.

Home in Becket

4.88 out of 5 average rating, 341 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Top guest favorite

The exterior of a two-story house is surrounded by lush greenery, featuring a large lawn and four red adirondack chairs positioned on the front porch. A clear blue sky with scattered clouds is visible above, providing a bright and inviting atmosphere.

Home in North Adams

5 out of 5 average rating, 109 reviews

Berkshires Retreat! in the woods, yet in town!

We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom vacation rental nested in 2.7 acres of woods, yet conveniently located in the city of North Adams. A 5 minute walk from Windsor Lake, a 15 minute walk to MASS MoCA, and a close drive to many restaurants. The house is kid friendly, basketball hoop, soccer goal, and games. We are close to ski resorts, as well hiking and biking trails, including Mount Greylock. PET FEE. PERMISSION NEEDED.

Guest favorite

A charming two-story house is surrounded by greenery, featuring a classic red exterior with white trim. A spacious porch runs along the front, while manicured grounds and a wooden fence enhance the property’s inviting appeal. Trees in the background provide a natural backdrop.

Home in Canaan

4.99 out of 5 average rating, 87 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

This newly updated Berkshire lake house with private in-ground pool, is the perfect place for a year-round vacation. Nestled within a small lakefront community where being on the lake is a pass-time in winter, spring, summer or fall. 6 light-filled bedrooms can accommodate a family retreat or 3 families. Enjoy the pool table, chefs kitchen, two living room areas, and wood burning fireplace inside and fire pit outside. All bedrooms and common areas have air conditioning.

Guest favorite

A hammock is suspended between two large trees, offering a serene spot to relax by the water. Below, colorful kayaks rest on the grassy shore, framing the edge of Glass Lake, which reflects the surrounding greenery and blue sky.

Home in Averill Park

4.98 out of 5 average rating, 174 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Age requirement of at least 30 years old for guests (except kids).

Top guest favorite

A private spa area features a jacuzzi surrounded by warm wood paneling and soft lighting. Steps lead down to the jacuzzi, enhancing accessibility. The space is designed for relaxation, conveying a serene ambiance with its clean lines and natural materials.

Home in Dover

4.98 out of 5 average rating, 141 reviews

Outdoor Paradise - Private Jacuzzi & Sauna

Enjoy the outdoors!! Located minutes from hiking, biking, kayaking and golf, this house has it all. You'll enjoy our spacious 4 bedroom / 3 bath private home in a quiet neighborhood with cathedral ceilings and open floor plan. Finished lower level with large screen TV and ping pong table give the kids space to spread out. Large deck has a huge gas grill and there is a stone fire pit in the back yard. You even have a private spa area with jacuzzi and sauna!

Guest favorite

The two-story farmhouse features a white exterior with dark shingles and light-colored shutters. A welcoming front entrance is highlighted by a small porch. Lush green grass and trees surround the home, enhancing its serene setting.

Home in Hudson

4.94 out of 5 average rating, 16 reviews

Kees Cottage

The best of all worlds! Beautifully remodeled 1910 farmhouse is mostly furnished with one-of-a-kind antiques, giving it a rustic, yet upscale vibe. Our large yard is magically peaceful and quiet, with a delightful hidden path leading to the pool and pool house. Amidst all this peace and privacy, you are still just 5 min. from the town of Hudson, with all of its boutiques, eateries, and culture. We offer 3 bedrooms and 1.5 baths, accommodating 6 guests.