Vacation rentals in Stamford

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Top-rated vacation rentals in Stamford

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Top guest favorite
A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.
Chalet in Stamford
4.93 out of 5 average rating, 115 reviews

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Top guest favorite
A red carriage house is set against a backdrop of mountains and blue skies. White Adirondack chairs circle a stone fire pit, while a picnic table and umbrella provide additional outdoor seating. Lush greenery surrounds the area, creating a serene environment.
Guesthouse in North Adams
5 out of 5 average rating, 301 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Top guest favorite
Guesthouse in North Bennington
4.99 out of 5 average rating, 304 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Top guest favorite
Apartment in North Adams
4.97 out of 5 average rating, 637 reviews

Steps to MoCA Near SKI: 2bd + SAUNA!

Near ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and others. A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 330 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.
Place to stay in North Adams
4.93 out of 5 average rating, 169 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Top guest favorite
A midcentury modern cabin is nestled among trees, its dark exterior contrasting with the fresh snow covering the ground. A spacious deck is visible, adorned with wooden railings, while large windows reflect the serene winter landscape.
Cabin in Shaftsbury
4.99 out of 5 average rating, 297 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Guest favorite
A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.
Apartment in Bennington
4.95 out of 5 average rating, 176 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 725 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Top guest favorite
A cozy bedroom is filled with natural light from two windows, dressed with blue curtains. A spacious bed with striped bedding is centered in the room. A white dresser and a television are positioned along the walls, creating a relaxing atmosphere.
Apartment in Stamford
4.87 out of 5 average rating, 334 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Escape to our cozy apartment in picturesque Southern Vermont! Featuring a comfortable bedroom, a well-equipped kitchenette, a private bathroom, and a charming dining area, this space has everything you need for a relaxing stay. Enjoy the perfect blend of tranquility and easy access—just a scenic 10-minute drive brings you to North Adams, MA, home to Mass MoCA, MCLA, and plenty of dining and shopping. Book now for the ideal balance of serenity and convenience!

Top guest favorite
The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.
Home in North Adams
4.99 out of 5 average rating, 153 reviews

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Top guest favorite
A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.
Cottage in Bennington
4.99 out of 5 average rating, 102 reviews

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Popular amenities for Stamford vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Stamford