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Holiday Homes in Stamford

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Stamford holiday homes

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

1. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is €173
includes taxes & fees
27 Sept - 28 Sept
Cozy Home in Pownal VT
A kitchen with white cabinets, a wooden dining table, and pendant lights.

2. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (60 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is €420
includes taxes & fees
5 Oct - 6 Oct
A roomy remodeled retreat close to MassMoCA
A two-story house with a porch, surrounded by trees and snow.

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is €320
includes taxes & fees
28 Sept - 29 Sept
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

4. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The Greylock Cabin
A red house with a porch, surrounded by a grassy yard and trees.

5. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is €377
includes taxes & fees
27 Sept - 28 Sept
Two Brooks Lodge
A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

6. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
Peaceful getaway at birds of a feather
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

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

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is €417
includes taxes & fees
28 Sept - 29 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

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

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (20 reviews)
"Great place!"
United States
Jack & Heather G.
The price is €499
includes taxes & fees
23 Sept - 24 Sept
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

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

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (114 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is €339
includes taxes & fees
23 Sept - 24 Sept
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

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

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is €584
includes taxes & fees
6 Oct - 7 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
An aerial view of a house surrounded by a forest with autumn foliage.

11. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is €550
includes taxes & fees
4 Oct - 5 Oct
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

12. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
Modern Mount Snow Gnarvana - Steps to Carinthia
A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

13. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A hallway with wooden flooring, white walls, and a bed in the background.

14. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is €318
includes taxes & fees
4 Oct - 5 Oct
Cozy private 2 bed apartment in Shelburne Falls
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (7 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
5BR Berkshire Home Mins To The Mountain
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
Private bed with En-suite bathroom Marigold Room
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

17. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (63 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
Walk To Town, Hottub, Firepit, Games, Mt Snow

18. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is €451
includes taxes & fees
23 Sept - 24 Sept
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

19. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is €567
includes taxes & fees
23 Sept - 24 Sept
Spacious 5BR w/ Hot Tub & Games
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

20. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is €682
includes taxes & fees
3 Oct - 4 Oct
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stamford Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place to stay in the Berkshires in the summer! Best price in the area for a busy weekend at Tanglewood. All other options were ridiculously expensive, Resort had great amenities. The indoor pool and outdoor hot tub where much appreciated after our trip out from the Boston area. Highly recommend this resort any time of year for ski season or summer/Fall sightseeing."
John 1-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

Find out more about Stamford

Stamford Holiday Homes information

Number of reviews
467
Accommodation
473 Holiday Homes
Lowest Price
€173
Highest Price
€682