Holiday Rentals in Stamford

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Our top choices for Stamford holiday rentals

3.0 star property
8.8 out of 10, Excellent, (2194)
"I great place to stay!!"
United Kingdom
Maricel
The price is €108
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is €196
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
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 €443
includes taxes & fees
4 Jan - 5 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is €261
includes taxes & fees
5 Jan - 6 Jan 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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 €212
includes taxes & fees
3 Jan - 4 Jan 2026
Berkshires Apartment at the Stephentown Hotel
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 €265
includes taxes & fees
2 Jan - 3 Jan 2026
Lake Whitingham & Mount Snow Area Village Apartment
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 €180
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is €381
includes taxes & fees
13 Jan - 14 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
Wilmington Retreat Near Trails, Skiing & Festivals
The price is €200
includes taxes & fees
13 Jan - 14 Jan 2026
Rose wisteria 4 guests 2 bedrooms-full+queen beds

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 €208
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
9.8 out of 10, Exceptional, (100)
"Beautiful, serene location with great penned in area for my lovable, niece pup! Spacious house with all the key amenities. Easy access for my elederly mom. "
United States
Lynn F.
The price is €267
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 €213
includes taxes & fees
2 Jan - 3 Jan 2026
Penthouse Apartment on Park Street
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 €442
includes taxes & fees
14 Jan - 15 Jan 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

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 €192
includes taxes & fees
4 Jan - 5 Jan 2026
Huttopia Berkshires

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 €317
includes taxes & fees
4 Jan - 5 Jan 2026
Florida Mountain Log Cabin
9.0 out of 10, Wonderful, (46)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is €267
includes taxes & fees
29 Jan - 30 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is €367
includes taxes & fees
12 Jan - 13 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is €415
includes taxes & fees
20 Jan - 21 Jan 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (4)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
United States
Chris I.
The price is €511
includes taxes & fees
4 Jan - 5 Jan 2026
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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

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, apart-hotels, 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 favorite 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 depends 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 €108 per night. Entering your travel dates in the search wizard you might find 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 Hopkins Observatory, 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.