Book Holiday Homes in Stamford

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Featured Holiday Homes in Stamford

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$368 per night from 4 Apr to 5 Apr
AU$368
includes taxes & fees
4 Apr - 5 Apr
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$420 per night from 13 Apr to 14 Apr
AU$420
includes taxes & fees
13 Apr - 14 Apr
Located in Shaftsbury, this vacation home is a 1-minute drive from Green Mountain National Forest and 6 minutes from Shaftsbury Historical Society Museum.
Peaceful Stay at Birds of a Feather Farm & Spa
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A River Retreat
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Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is AU$1,675 per night from 4 Apr to 5 Apr
AU$1,675
includes taxes & fees
4 Apr - 5 Apr
With a stay at this vacation home in Pittsfield, you'll be on the waterfront, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Hancock Village Inn at Jiminy Peak
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Shaftsbury
A stay at this vacation home places you in the heart of Shaftsbury, steps from Green Mountain National Forest and 13 minutes by foot from Robert Frost Stone ...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
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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.

Stamford Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Stamford vacation homes are the perfect way for you to wing it.

Holiday houses in Stamford let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Stamford in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Stamford adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Stamford with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Stamford vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Stamford Holiday Homes essential information

Accommodation
483 Holiday Homes
Lowest Price
AU$196
Highest Price
AU$1,675
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Peaceful Stay at Birds of a Feather Farm & Spa , The Jelly Mill-A River Retreat, Hancock Village Inn at Jiminy Peak, Cozy Converted Barn on Secluded 6.5 acres with Hot Tub, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!

Top trending hotels in Stamford

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$379 per night from 6 Apr to 7 Apr
AU$379
includes taxes & fees
6 Apr - 7 Apr
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
The Williams Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 13 Apr to 14 Apr
AU$225
includes taxes & fees
13 Apr - 14 Apr
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 20 Apr to 21 Apr
AU$226
includes taxes & fees
20 Apr - 21 Apr
A stay at Hotel Downstreet, Ascend Hotel Collection places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Hotel Downstreet, Ascend Hotel Collection
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Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 6 Apr to 7 Apr
AU$196
includes taxes & fees
6 Apr - 7 Apr
When you stay at Mountaineer Inn in West Dover, you'll be near ski lifts, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Mountaineer Inn
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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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^Subject to availability and chosen travel dates.