Stamford Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Stamford vacation rentals

1. Vacation Village in the Berkshires

Williamstown

Marcos

￥15,862 total

includes taxes & fees

Nov 19 - Nov 20

A kitchen with white cabinets, a wooden dining table, and pendant lights.

2. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

￥73,921 total

includes taxes & fees

Nov 10 - Nov 11

A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

3. Greylock Cabin

Florida

Margaret M.

￥76,323 total

includes taxes & fees

Nov 10 - Nov 11

A cozy living room with a TV, a bookshelf, and a window with a view of greenery.

4. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Pownal

Claudette R.

￥93,133 total

includes taxes & fees

Nov 11 - Nov 12

"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

5. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

￥47,905 total

includes taxes & fees

Nov 15 - Nov 16

A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

6. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

￥32,546 total

includes taxes & fees

Nov 9 - Nov 10

"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

7. 2-Bdr Apt In Town, By the Water

Williamstown

Thomas

￥46,948 total

includes taxes & fees

Nov 9 - Nov 10

A log cabin with a balcony, surrounded by trees.

8. Bear Creek Cabin

Charlemont

Hillary S.

￥90,070 total

includes taxes & fees

Nov 10 - Nov 11

9. New Studio In Town, By the Water

Williamstown

Lydia J.

￥43,956 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

10. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham

Nicole H.

￥118,234 total

includes taxes & fees

Nov 12 - Nov 13

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

11. Cozy Home in Pownal VT

Pownal

Jeri R.

￥30,709 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

12. Penthouse Apartment on Park Street

Adams

Margaret C.

￥42,043 total

includes taxes & fees

Nov 9 - Nov 10

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

￥85,553 total

includes taxes & fees

Nov 22 - Nov 23

A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

14. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Hoosick Falls

cory p.

￥59,278 total

includes taxes & fees

Nov 11 - Nov 12

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

15. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

Natalie

￥85,487 total

includes taxes & fees

Nov 11 - Nov 12

A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

16. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Charlemont

Georgia P.

￥198,457 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

17. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

Dana W.

￥82,198 total

includes taxes & fees

Nov 9 - Nov 10

A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

18. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Wilmington

Mark

A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

19. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Whitingham

Ben B.

￥96,484 total

includes taxes & fees

Nov 9 - Nov 10

A house with a garage, surrounded by snow-covered trees and a mountain in the background.

20. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Whitingham

Jonathan

￥76,200 total

includes taxes & fees

Nov 11 - Nov 12

View all properties

Find vacation rentals that suit your style

Top Stamford Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Stacey

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Sandra

A fire feature with a metal frame and a brick wall in the background.

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

10/10 Excellent

Diane

A wooden sign with an arrow pointing to the right, labeled "CHICKENS".

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

A kitchen with a countertop, a refrigerator, and a window.

The Villager Motel

Williamstown

10/10 Excellent

Anonymous traveler

A large, two-story house with a covered porch and multiple chimneys.

The Four Chimneys Inn

Bennington

10/10 Excellent

Randall

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

A modern living room with a fireplace, large windows, and a cozy seating area.

Inn At Mount Snow

West Dover

10/10 Excellent

Peter

A snow-covered gazebo with a clear view of the surrounding trees and a bright sun in the background.

Harwood Hill Motel

Bennington

10/10 Excellent

We stayed here for one overnight while visiting the area. The hotel was just what we were looking for - affordable, clean, great location. There is a restaurant right next door and an apple picking orchard across the street. Easy 5-10 minute drive to a few other restaurants and about 30 minutes from Manchester with great shopping and hiking. The free breakfast in the morning was also great. I would recommend it!

Allison

A spacious kitchen with large windows, a bar area, and a dining setup with chairs and tables.

The White House Inn

Wilmington

10/10 Excellent

Rya

A living room with a fireplace, two sofas, and four black side tables.

The Revival House

Adams

10/10 Excellent

Katrina

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

Find out more about Stamford

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Frequently Asked Questions

Can I find a vacation rental in Stamford?

Yes, there are vacation rentals near the most popular attractions in Stamford, or you can select a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Stamford?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This vacation home rental outside of Stamford is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Stamford?

Expedia has 4 vacation rentals for your stay in Stamford.

What’s there to see and do in Stamford?

While exploring the area, visit family-friendly sights like Buzzy Park, or get outside and enjoy nature at Green Mountain National Forest. While here, Stamford Town Hall and Clarksburg State Park are other places worth a visit.

What’s a vacation rental in Stamford like?

Vacation rentals are private accommodations you can reserve for several days or longer in Stamford. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.

Stamford Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stamford vacation rentals

1. Vacation Village in the Berkshires

2. A roomy remodeled retreat close to MassMoCA

3. Greylock Cabin

4. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

5. Downtown | Waterfront | Walk to Shops

6. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

7. 2-Bdr Apt In Town, By the Water

8. Bear Creek Cabin

9. New Studio In Town, By the Water

10. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

11. Cozy Home in Pownal VT

12. Penthouse Apartment on Park Street

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

14. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

15. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

16. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

17. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

18. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

19. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

20. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Find vacation rentals that suit your style

Top Stamford Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

Find out more about Stamford

Frequently Asked Questions

Can I find a vacation rental in Stamford?

What's the top vacation rental in Stamford?

How many vacation rentals are there in Stamford?

What’s there to see and do in Stamford?

What’s a vacation rental in Stamford like?