Stamford Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Stamford

Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (858)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is HK$1,230
per night
3 Jun - 4 Jun
Jiminy Peak Mountain Resort
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (116)
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (13)
"Had such a wonderful stay in the beautiful Berkshires at this unique cabin property! Everything was clean and well-maintained. Very rustic and charming. We had a lot of fun by the fire and walking down to the river in the backyard. So many things to do in this area! Hiking, rafting, and dining in the nearby towns! Would definitely return!"
The price is HK$3,125
per night
28 May - 29 May
Bear Creek Cabin
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (37)
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
TV
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (14)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (91)
"Wonderful property for family and dog!"
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (65)
"I absolutely loved this property! It was immaculate and had everything someone would need. The bed was very comfortable as was the living room furniture. I loved sitting out on the deck at night and watching the deer. The fire pit and the hot tub are a bonus. I enjoyed my stay and can’t wait to return."
Hearts Desire is a furnished whole house in a small, colorful garden center.
Fridge, microwave, oven, stovetop
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very good, (19)
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (39)
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (18)
"This location was great. Having the clubhouse with access to the pool is an added bonus. We would definitely book again in the future."
The price is HK$578
per night
28 May - 29 May
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Pool
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, (28)
"Overall property was good, and the unit was very good. Our needs were minimal, but if we had questions, Tiago was very quick and to respond."
Walk to Mount Snow, Cozy, Clean and Comfortable!
Don't see what you're looking for?
See all available properties in Stamford
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.

Other types of properties in Stamford you may be interested in

Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (923)
"A great place to stay in North Adams. Clean, friendly and located just a couple of miles from an outstanding breakfast restaurant. "
The price is HK$1,118
per night
9 Jun - 10 Jun
Hotel Downstreet
Fireplace
Mountaineer Inn
2.0 star property
9.2 out of 10, Wonderful, (289)
"Loved that this is a legit old ski lodge and still has the feel while having modernized what needed to be. Loved it here."
The price is HK$963
per night
30 May - 31 May
Mountaineer Inn
Front of property – evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (294)
"Love the Williams Inn"
The price is HK$2,056
per night
25 Jun - 26 Jun
The Williams Inn
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.

Search for holiday rentals in Stamford on Expedia! You can easily find your home rentals, villas, holiday apartments in Stamford using one of the methods below:

  • View our selection of featured holiday rentals in Stamford
  • Use the map to find apartments and other holiday homes in the Stamford neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Stamford while they last

Look no further and take a look at our great range of rental properties in Stamford!

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?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This holiday home rental outside of Stamford is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 Clarksburg State Park. In the wider area, you’ll find Natural Bridge State Park and Massachusetts Museum of Contemporary Art.

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.

Recent reviews of Stamford properties
Expedia verified reviews

Hampton Inn Bennington

Hampton Inn Bennington

5/5 Excellent
"Not many things to do. "
A verified traveller stayed at Hampton Inn Bennington
Posted 3 days ago
Hampton Inn Bennington