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Holiday Homes in Stamford

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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 AU$300
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A bedroom with a bed, bedside tables, a window, and a radiator.

2. 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 AU$608
includes taxes & fees
13 Oct - 14 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A kitchen with white cabinets, a wooden dining table, and pendant lights.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AU$680
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

4. Greylock Cabin

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 price is AU$643
includes taxes & fees
8 Nov - 9 Nov
Greylock Cabin
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$311
includes taxes & fees
8 Nov - 9 Nov
Private bed with En-suite bathroom Marigold Room
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

6. 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, (115 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 AU$557
includes taxes & fees
20 Oct - 21 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

7. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AU$812
includes taxes & fees
26 Oct - 27 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

8. 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 AU$898
includes taxes & fees
13 Oct - 14 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

9. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AU$227
includes taxes & fees
20 Oct - 21 Oct
The Eagles Wing at The CHM - Private Apartment
An aerial view of a house surrounded by a forest with autumn foliage.

10. 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 AU$767
includes taxes & fees
28 Oct - 29 Oct
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AU$933
includes taxes & fees
2 Nov - 3 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

12. 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.
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Pool

13. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.6 out of 10, Excellent, (11 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 AU$768
includes taxes & fees
12 Oct - 13 Oct
Comfortable Berkshires retreat on mtn resort, SISO
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.

14. 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 hallway with wooden flooring, white walls, and a bed in the background.

15. 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 AU$600
includes taxes & fees
12 Oct - 13 Oct
Cozy private 2 bed apartment in Shelburne Falls
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is AU$1,156
includes taxes & fees
13 Oct - 14 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

17. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AU$1,086
includes taxes & fees
13 Oct - 14 Oct
5BR Berkshire Home Mins To The Mountain
A wooden barrel structure with a staircase and railing, surrounded by a forest.

18. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is AU$971
includes taxes & fees
1 Nov - 2 Nov
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
A wooden deck with a table and chairs, surrounded by a white railing.

19. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AU$696
includes taxes & fees
13 Oct - 14 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

20. 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 AU$1,019
includes taxes & fees
13 Oct - 14 Oct
Spacious 5BR w/ Hot Tub & Games
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

The White House Inn

The White House Inn

8/10 Good
"We had dinner there and it was excellent. Breakfast was disappointing."
Robert 1-night trip
Posted 3 hours ago
The White House Inn

Find out more about Stamford

Stamford Holiday Homes information

Number of reviews
423
Accommodation
471 Holiday Homes
Lowest Price
AU$227
Highest Price
AU$1,156