Vacation rentals in Stamford

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Top-rated vacation rentals in Stamford

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Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 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.

Dec 12 – 19

G$19,898 GYD per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Apr 12 – 19

G$29,236 GYD per night

Guest favorite

Guesthouse in North Bennington

4.98 out of 5 average rating, 150 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 light space with 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. Please note that due to a severe allergy, we cannot accommodate animals.

Oct 23 – 30

G$32,660 GYD per night

Guest favorite

Apartment in Bennington

4.96 out of 5 average rating, 139 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.

Jul 24 – 31

G$25,865 GYD per night

Guest favorite

Guesthouse in North Adams

4.92 out of 5 average rating, 181 reviews

"Worker's" Cottage (circa 1860).

Escape to Berkshires in our renovated, classic "Worker's" cottage (circa 1860) style townhouse. Close to Vermont & New York State. Downtown North Adams & Williamstown all offer excellent Museums, dining, shopping, and outdoor recreation. Several ski resorts to choose from including Jiminy Peak, Mount Snow, Berkshire East (all under an hour from the house) and Stratton (about 1 hr 20 min depending on the weather). We look forward to hosting you!

Jun 8 – 15

G$25,147 GYD per night

Guest favorite

Home in North Adams

4.99 out of 5 average rating, 266 reviews

Steps to MoCA near SKI private house + SAUNA!

20-30 mins to Jiminy Peak, East Mountain, Prospect Ski. 50 mins to Mount Snow. Tucked away on a hilltop oasis right above MoCA (3 mins by walk) the whimsically restored house is part of an private estate that belonged to the owners of APW factory (now the museum). Steps to downtown & restaurants. 10 min drive to Williams & Clark. Now part of a retreat for immigrant & refugee musicians: your stay enables us to host artists pro bono.

Dec 23 – 30

G$31,843 GYD per night

Guest favorite

Apartment in Bennington

4.91 out of 5 average rating, 163 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Aug 22 – 29

G$21,008 GYD per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Jul 29 – Aug 5

G$20,310 GYD per night

Guest favorite

Apartment in Pownal

4.94 out of 5 average rating, 179 reviews

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).

May 3 – 10

G$22,678 GYD per night

Guest favorite

Guesthouse in Williamstown

4.97 out of 5 average rating, 146 reviews

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.

Aug 25 – Sep 1

G$27,521 GYD per night

Superhost

Cabin in Readsboro

4.85 out of 5 average rating, 186 reviews

Off grid comfort cabin

Rustic mountain cabin with taste and comfort in mind.,outdoor portable toilet.outdoor shower with hot water,indoor gas range.,outdoor gas grill,fire pit and a loft with bunk beds and a double bed . A rap around deck half with roof ,off rd parking,hiking,skimobiling,wildlife on propriety swimming near by no electricity

Jun 10 – 17

G$14,377 GYD per night

Guest favorite

Home in Shaftsbury

4.92 out of 5 average rating, 103 reviews

Cheerful 1 bedroom cottage

Located one mile from the historic village of North Bennington, this newly renovated one bedroom, one bath (with full kitchen) affords all the comforts of home while providing easy access to both Bennington College (within two miles) and the many attractions of the surrounding area.

Nov 4 – 11

G$17,416 GYD per night