Book Holiday Homes in Stamford
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Featured Holiday Homes in Stamford

Charming Berkshires Retreat – Minutes to Williamstown

The Jelly Mill-A Peaceful River Retreat

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

2 Mi to Hoosic River: 'The Moss House' w/ Deck!

Contemporary Berkshire Home with Views of Taconic Golf Course

Private Family Estate for any Season

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
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 | 513 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Charming Berkshires Retreat – Minutes to Williamstown, The Jelly Mill-A Peaceful River Retreat, Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, 2 Mi to Hoosic River: 'The Moss House' w/ Deck!, Contemporary Berkshire Home with Views of Taconic Golf Course, Private Family Estate for any Season, Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort.., Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax! |
Top Locations for Holiday Homes in Stamford
More accommodations in Stamford
Top trending hotels in Stamford

Vacation Village in the Berkshires

Hotel Downstreet, Ascend Hotel Collection

The Williams Inn

Hotel Vervana, Trademark Collection by Wyndham
More ways to explore Stamford
Top picks
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^Subject to availability and chosen travel dates.