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Stamford Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Stamford vacation rentals

Exterior

1. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (34 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is CA $94
CA $198 total
includes taxes & fees
Sep 14 - Sep 15
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Interior

2. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Outdoor dining

3. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is CA $166
CA $371 total
includes taxes & fees
Sep 14 - Sep 15
New Studio In Town, By the Water
Outdoor dining

4. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is CA $171
CA $385 total
includes taxes & fees
Sep 14 - Sep 15
Downtown | Waterfront | Walk to Shops
Outdoor dining

5. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
8.8 out of 10, Excellent, (18 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is CA $166
CA $390 total
includes taxes & fees
Sep 14 - Sep 15
2-Bdr Apt In Town, By the Water
Dining

6. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (8 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is CA $149
CA $267 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Home in Pownal VT
Dining

7. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is CA $318
CA $671 total
includes taxes & fees
Sep 15 - Sep 16
A roomy remodeled retreat close to MassMoCA
Lobby

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,636 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is CA $132
CA $163 total
includes taxes & fees
Sep 15 - Sep 16
Vacation Village in the Berkshires
Living area

9. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is CA $201
CA $387 total
includes taxes & fees
Sep 14 - Sep 15
Penthouse Apartment on Park Street
Exterior

10. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Outdoor pool, a heated pool

11. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is CA $67
CA $415 total
includes taxes & fees
Sep 14 - Sep 15
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

12. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge
Exterior

13. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is CA $426
CA $692 total
includes taxes & fees
Oct 7 - Oct 8
The Greylock Cabin
Exterior

14. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is CA $281
CA $622 total
includes taxes & fees
Sep 17 - Sep 18
North Getaway Cottage
Dining

15. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is CA $272
CA $780 total
includes taxes & fees
Sep 14 - Sep 15
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Interior

16. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
The price is CA $161
CA $375 total
includes taxes & fees
Sep 15 - Sep 16
Peaceful getaway at birds of a feather
Dining

17. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is CA $403
CA $831 total
includes taxes & fees
Sep 15 - Sep 16
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Exterior

18. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is CA $220
CA $607 total
includes taxes & fees
Sep 21 - Sep 22
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Property grounds

19. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is CA $134
CA $309 total
includes taxes & fees
Sep 14 - Sep 15
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Private kitchen

20. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (5 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is CA $156
CA $336 total
includes taxes & fees
Sep 30 - Oct 1
The Studio with a View. Bring your dog, too!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My go-to place for visiting NW MA."
David 1-night trip
Posted 11 hours ago
Vacation Village in the Berkshires

Find out more about Stamford

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stamford vacation rentals we have selected for you start as low as CA $163 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 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?

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views: Visitors like this Stamford vacation home rental. It offers a fireplace and WiFi to help you feel comfortable in your new surroundings. Kitchen amenities include a stovetop to make your meal-planning easier.

How many vacation rentals are there in Stamford?

Expedia has 4 vacation 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, Stamford Town Hall and Clarksburg State Park are other places worth a visit.

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.