Stamford Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stamford holiday rentals

10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is AU$220
includes taxes & fees
20 Dec - 21 Dec
Getaway Near Mass MoCA, Great Hiking, Scenic Views
3.0 star property
8.8 out of 10, Excellent, (2178)
"Awesome for ski"
United States
Lazar
The price is AU$192
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is AU$490
includes taxes & fees
5 Jan - 6 Jan 2026
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is AU$370
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is AU$465
includes taxes & fees
20 Dec - 21 Dec
Lake Whitingham & Mount Snow Area Village Apartment
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is AU$686
includes taxes & fees
5 Jan - 6 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
The price is AU$316
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Rustic Apt in 18th c Berkshire Farmhouse
The price is AU$231
includes taxes & fees
5 Jan - 6 Jan 2026
2 Twin beds on 1st floor with En-suite bathroom.
10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AU$434
includes taxes & fees
21 Dec - 22 Dec
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is AU$435
includes taxes & fees
21 Dec - 22 Dec
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is AU$858
includes taxes & fees
5 Jan - 6 Jan 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AU$762
includes taxes & fees
13 Jan - 14 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (100)
"Quiet and relaxing property "
United States
Michelle S.
The price is AU$499
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is AU$787
includes taxes & fees
13 Jan - 14 Jan 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$518
includes taxes & fees
23 Dec - 24 Dec
Florida Mountain Log Cabin

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is AU$327
includes taxes & fees
4 Jan - 5 Jan 2026
Huttopia Berkshires
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is AU$347
includes taxes & fees
23 Dec - 24 Dec
Berkshires Apartment at the Stephentown Hotel
9.0 out of 10, Wonderful, (44)
"We were unable to stay as when we went in the condo, we found the condo damp, musty, dusty, very worn, extremely outdated and uncomfortable. We left and found different accommodations for the weekend at Chateau 239 which I highly recommend. "
United States
Diana W.
The price is AU$469
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AU$374
includes taxes & fees
23 Dec - 24 Dec
Penthouse Apartment on Park Street

Apartment in Bennington

Green Mountain Getaway
2.0 star property
9.6 out of 10, Exceptional, (18)
"Great Location -- place was spotless and very accommodating"
United States
Michael H.
The price is AU$570
includes taxes & fees
4 Jan - 5 Jan 2026
Green Mountain Getaway
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stamford Hotel Reviews

Find out more about Stamford

Everything you need to know about Stamford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stamford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stamford holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Stamford holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stamford. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stamford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stamford holiday rentals we have selected for you start as low as AU$192 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Stamford rentals

At Expedia, we put the best Stamford holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stamford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stamford holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stamford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Stamford?

Yes, there are holiday rentals close to the most popular sights in Stamford, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Stamford has to offer?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of Stamford is located in the mountains, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals are there in Stamford?

Expedia has 3 holiday rentals for your stay in Stamford.

What’s there to see and do in Stamford?

While exploring the area, visit family-friendly sights like Southern Vermont Natural History Museum, or get outside and enjoy nature at Green Mountain National Forest. While here, Clarksburg State Park and Stamford Town Hall are other places worth a visit.

What’s a holiday rental in Stamford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Stamford. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.