Holiday houses in Stamford

4.92 out of 5 average rating, 100 reviews

Chalet in Stamford

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).

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Cabin in Clarksburg

4.9 out of 5 average rating, 282 reviews

Mountain Cottage Spectacular Views

This lovely cottage sits on 90 acres featuring gardens, fruit groves, forest, and the Hoosic River. Spectacular views of Mt Greylock. Truly an idyllic location, the perfect retreat for a lover of the outdoors but also close to cultural offerings. Less than 10 minutes to downtown North Adams and Mass MOCA. Williamstown and the Clark Art Institute are nearby as well. Plenty of long or short hikes, scenic walks and bike rides as well as local restaurants and shops that are easily accessible.

Guesthouse in North Bennington

4.99 out of 5 average rating, 254 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 animal

Guest suite in Williamstown

4.96 out of 5 average rating, 239 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Apartment in Williamstown

4.94 out of 5 average rating, 101 reviews

Williamstown apt close to Williams College & MoCA.

Second floor 1 bedroom (Queen) and 1 bathroom apartment with private entrance. This cozy Williamstown retreat will provide exactly what you would expect in the Berkshires. Walking distance to downtown Williamstown and the newly created bike path. This unit provides off street parking with plenty of privacy, and can truly transform your stay. Less than 5 Miles to MASS MoCA. 25 Minutes to Jiminy Peak. 1.5 Miles exactly to the center of Spring St. .4 Miles to the bike path entrance.

4.95 out of 5 average rating, 165 reviews

Apartment in Bennington

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.

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Cottage in Monroe

4.87 out of 5 average rating, 135 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

4.87 out of 5 average rating, 313 reviews

Apartment in Stamford

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!

4.92 out of 5 average rating, 109 reviews

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

Experience North Adams with unbeatable convenience! This centrally located apartment puts your whole group just a short walk or bike ride away from Mass MoCA, the farmer’s market, and the shops and restaurants on Main Street. Enjoy stress-free access to all the local attractions—no parking hassles, just easy, enjoyable days exploring the best of North Adams. Perfect for your next Mass MoCA event or weekend getaway!

4.85 out of 5 average rating, 542 reviews

Guesthouse in Pownal

Bauhaus Guest House in So. VT.

Enter through a flowering courtyard into this one room studio style guest house with full bath, closet and sliding glass doors looking out upon a lush green landscape in Southern Vermont. Parking, wi-fi and local insight included. Hosts = AMAZING :) 5 miles to Williamstown Theater Festival, Williamstown, MA 9 miles to Mass MoCA, North Adams, MA 9 miles to Bennington, VT

4.94 out of 5 average rating, 199 reviews

Apartment in Pownal

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

4.97 out of 5 average rating, 563 reviews

Steps to MoCA: 2bd + SAUNA!

A large and private 2 bedroom apt at the Small Mansion of Chase Hill, 3 mins by walk to Mass MoCA. 10 mins drive to Williams College, Clark. 5 mins walk to downtown’s restaurants. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat YOUR STAY HERE ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

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Other great holiday rentals in Stamford

4.96 out of 5 average rating, 73 reviews

Cabin in Guilford

Guilford Grove Cottage

JulieRating, 5 stars1 week ago

Joel's place was impeccably clean and free of clutter. The shower pressure was excellent. The kitchen had everything you need ro cook, and it was a treat to have milk, eggs, english muffins and coffee available for breakfast as well as tea which you can enjoy sitting out on the porch. It is a short drive to Brattleboro and the surrounding area is exquisitely beautiful.

4.83 out of 5 average rating, 60 reviews

Walnut Way basement apartment

BenRating, 5 stars1 month ago

It was bigger in person! Easy check in, check out. Megan was easy to communicate with.

4.95 out of 5 average rating, 74 reviews

"Nostalgia" a spacious2 bedroom first floor unit.

Gary And HeidiRating, 5 stars1 week ago

We had a good time staying at Sandy‘s place. It was exactly what we needed for a graduation weekend. Really appreciated the extra touch of coffee and tea as well as creamer, a thoughtful touch! It easy to work with Sandy. She was responsive to all my messages.

4.98 out of 5 average rating, 41 reviews

Cottage in Pownal

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

HedyRating, 5 stars6 days ago

outstanding! we stayed for over a week to be close to Williamstown, which was only a 10 minute drive as promised. Beautiful quiet setting, quick responses to any questions, and a well-appointed cottage with all the necessary amenities. hope to stay here in future.

5 out of 5 average rating, 30 reviews

Home in Woodford

Bright airy cottage w/ lake view

TammyRating, 5 stars6 days ago

Girls weekend trip away, very serene. Beds/linens were comfortable , loved the sunroom!! Enjoyed my cup of coffee in the morning looking out into the woods.

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Home in Clarksburg

4.85 out of 5 average rating, 68 reviews

New & Cozy~Near MoCa~Deck~River

ChuckRating, 5 stars1 week ago

This is a delightful place! It's very near town but off the road so it's quiet. The house is larger than I expected and extremely tranquil and restorative. The sound of the creek just outside the porch is incredible! And Marin was a lovely and responsive host. Highly recommend.

5 out of 5 average rating, 33 reviews

Barn in Florida

The Red Barn- close to ski mountains & museums

LucyRating, 5 stars1 week ago

Easy, breezy, no fuss experience for a 3 day work trip in June with spouse and 2 y.o. in tow. Great private location for a stompy, chatty toddler. We were barely at the place, but everything was easy and straight forward. On a cool night, the breeze from the window is lovely. Very responsive and helpful host, nothing was complicated.