Stamford Vacation Rentals

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Vacation Rentals in Stamford

Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $154
$169 total
includes taxes & fees
Jun 20 - Jun 21
Jiminy Peak Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (25)
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (118)
"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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, (17)
"Definitely recommend this place for large groups. Very clean, so much to do, and great communication with host. Very private location"
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
8.8 out of 10, Excellent, (38)
"The home location, layout were awesome. Pics must be older as there was maintenance needed on the basketball/tennis court, pool, and shuffleboard room. Our bachelor party had a good time, once some updates are done, could be a 5 start spot."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (206)
"What an amazing place Lars shared with us for a few days. What a peaceful and fun place- very homey! We enjoyed watching the rabbits and the bear wandering the property from the spacious hot tub- great ways to enjoy any evening. Thanks again"
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Bear Creek Cabin
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (14)
"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"
The price is $400
$607 total
includes taxes & fees
Jun 23 - Jun 24
Bear Creek Cabin
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (206)
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
Dog-friendly chalet cabin with valley view, deck, and private hot tub
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
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
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
The Brown House. Indoor pool - Spa - Sauna - Gameroom
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
Mount Snow's Best View - Sleeps 8-10
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
Jacksonville Cabin w/ Wraparound Deck & Views
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
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (19)
"Good Condo in a great location"
The price is $74
$338 total
includes taxes & fees
Jun 21 - Jun 22
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Walk to Mount Snow, Cozy, Clean and Comfortable!
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!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (36)
"The house was perfect for our larger family event. The bedrooms were quiet and each one had their own bathroom. The owner was responsive to any needs. We had a wonderful event."
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Great Place to get away and have clean fresh air surround you!
Exterior
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (121)
"The house has a beautiful view of the lake and is very clean. It is beautifully decorated, and has all the supplies that are needed for comfortable stay. The owner is very thoughtful and the house is nicely organized. We appreciated the Christmas decorations during our holiday stay, extra towels prepared for the dog and the dog treats. The house is nicely stocked with family games, and there is beautiful trail in walking distance: up the hill to vast trail, and path through the forest to Little...
Great Place to get away and have clean fresh air surround you!
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (35)
"We live in three different states and are usually only all together once a year at the oldest sister’s house. This year we decided to go away together after attending a graduation party. Lots of time to talk and laugh! This house was perfect for that!"
Cozy Cottage Along Idyllic Green River
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

Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (930)
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."
The price is $134
$150 total
includes taxes & fees
Jun 23 - Jun 24
Hotel Downstreet
Mountaineer Inn
Fireplace
Mountaineer Inn
2.0 star property
9.2 out of 10, Wonderful, (291)
"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 $113
$131 total
includes taxes & fees
Jun 20 - Jun 21
Mountaineer Inn
The Williams Inn
Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (305)
"Wonderful stay and meal was very yummy. Even though waiter said we ordered too my co. But we were hungry. "
The price is $262
$293 total
includes taxes & fees
Jun 26 - Jun 27
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.

Everything you need to know about Stamford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stamford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stamford vacation 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 low season months. For more hustle and bustle, you may prefer to visit Stamford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stamford rentals

At Expedia, we put the best Stamford vacation 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 vacation.

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 vacation rental in Stamford?

Yes, there are vacation rentals near the most popular attractions in Stamford, or you can select a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Stamford?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This vacation home rental outside of Stamford is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area, you’ll find Mount Snow and Massachusetts Museum of Contemporary Art.

What’s a vacation rental in Stamford like?

Vacation rentals are private accommodations you can reserve for several days or longer in Stamford. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.

Recent reviews of Stamford properties
Expedia verified reviews

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

5/5 Excellent
"Nice stay. It’s our third visit."
A verified traveler stayed at Club Wyndham Bentley Brook
Posted 20 hours ago
Club Wyndham Bentley Brook