Book Holiday Homes in Stamford

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Featured Holiday Homes in Stamford

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Crane Museum of Papermaking and Barrington Stage ...
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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 NY
Stay at this holiday home in Hoosick Falls. Enjoy free Wi-Fi, breakfast (surcharge) and a garden. Popular attractions Bennington Center for the Arts and Bennington ...
Opens in a new windowCozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Charming Berkshire Retreat-Minutes to Williamstown

Charming Berkshire Retreat-Minutes to Williamstown

Williamstown MA
Stay at this holiday home in Williamstown. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Green River Wildlife Management Area and Brodie ...
Opens in a new windowCharming Berkshire Retreat-Minutes to Williamstown
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Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown MA
Stay at this holiday home in Williamstown. Enjoy a garden, laundry facilities and patios. Popular attractions Williams College Taconic Golf Course and Lunder ...
Opens in a new windowContemporary Berkshire Home with Views of Taconic Golf Course
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
Stay at this holiday home in Cheshire. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mount Greylock State Reservation Visitor Center ...
Opens in a new window19th c. Barn in the Berkshires
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

Williamstown MA
Stay at this family-friendly holiday home in Williamstown. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Lower Linear Park and Cole ...
Opens in a new window3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

Guilford VT
Stay at this holiday home in Brattleboro. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Sweet Pond State Park and Leyden State Forest ...
Opens in a new windowThe Jelly Mill-A Peaceful River Retreat
Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Shelburne Falls MA
Stay at this holiday home in Shelburne Falls. Enjoy a garden, laundry facilities and cable/satellite TV service. Popular attractions Bald Mountain Pottery and ...
Opens in a new windowStylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.
Secluded Family Getaway w/ On-Site Creek in Hawley

Secluded Family Getaway w/ On-Site Creek in Hawley

Hawley MA
Stay at this holiday home in Charlemont. Enjoy a garden, patios and an in-room coffee maker. Popular attractions Hawley Bog Preserve and Hail to the Sunrise ...
Opens in a new windowSecluded Family Getaway w/ On-Site Creek in Hawley
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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
427 Holiday Homes
Lowest Price
NZ$180
Highest Price
NZ$554
Popular accommodation
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!, Charming Berkshire Retreat-Minutes to Williamstown, Contemporary Berkshire Home with Views of Taconic Golf Course, 19th c. Barn in the Berkshires, 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome, The Jelly Mill-A Peaceful River Retreat, Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village., Secluded Family Getaway w/ On-Site Creek in Hawley

Top trending hotels in Stamford

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 NZ$180 per night from 11 May to 12 May
NZ$180
11 May - 12 May
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is NZ$266 per night from 13 May to 14 May
NZ$266
13 May - 14 May
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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 NZ$554 per night from 11 May to 12 May
NZ$554
11 May - 12 May
includes taxes & fees
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Williams Inn
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The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street North Adams MA
Fully refundableReserve now, pay when you stay
The price is NZ$373 per night from 11 May to 12 May
NZ$373
11 May - 12 May
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowThe Porches Inn at Mass MoCA
Don't see what you're looking for?
See all available properties in Stamford
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.