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Stamford Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Stamford holiday 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, (35 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 HK$529
HK$1,120 total
includes taxes & fees
16 Sept - 17 Sept
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.
The price is HK$777
HK$1,647 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$941
HK$2,029 total
includes taxes & fees
16 Sept - 17 Sept
New Studio In Town, By the Water
Outdoor dining

4. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (19 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 HK$941
HK$2,223 total
includes taxes & fees
16 Sept - 17 Sept
2-Bdr Apt In Town, By the Water
Outdoor dining

5. 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 HK$965
HK$2,196 total
includes taxes & fees
16 Sept - 17 Sept
Downtown | Waterfront | Walk to Shops
Dining

6. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (59 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is HK$1,796
HK$3,767 total
includes taxes & fees
16 Sept - 17 Sept
A roomy remodeled retreat close to MassMoCA
Dining

7. 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 HK$840
HK$1,459 total
includes taxes & fees
27 Sept - 28 Sept
Cozy Home in Pownal VT
Lobby

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,645 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is HK$746
HK$919 total
includes taxes & fees
17 Sept - 18 Sept
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 HK$1,137
HK$2,102 total
includes taxes & fees
19 Sept - 20 Sept
Penthouse Apartment on Park Street
Exterior

10. 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 HK$1,101
HK$3,244 total
includes taxes & fees
16 Sept - 17 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Exterior

11. 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
The price is HK$1,090
HK$3,227 total
includes taxes & fees
20 Sept - 21 Sept
Two Brooks Lodge
Exterior

12. 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 Greylock Cabin
Pool

13. 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 HK$424
HK$2,393 total
includes taxes & fees
21 Sept - 22 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dining

14. 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 HK$2,276
HK$4,674 total
includes taxes & fees
16 Sept - 17 Sept
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Property grounds

15. 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 HK$755
HK$1,755 total
includes taxes & fees
16 Sept - 17 Sept
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Dining

16. 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 HK$1,537
HK$4,478 total
includes taxes & fees
16 Sept - 17 Sept
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Gift shop

17. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is HK$1,043
HK$2,129 total
includes taxes & fees
20 Sept - 21 Sept
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Interior

18. 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 HK$939
HK$2,150 total
includes taxes & fees
21 Sept - 22 Sept
Peaceful getaway at birds of a feather
Beach

19. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is HK$706
HK$2,322 total
includes taxes & fees
22 Sept - 23 Sept
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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

Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"One of the friendliest staffs I have ever encountered. The room was more than up to snuff, and the location was very convenient."
Lucas 2-night trip
Posted 16 hours ago
Willows Motel Williamstown

Find out more about Stamford

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:

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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?

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views: This highly rated holiday home rental in Stamford 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 holiday rentals are there in Stamford?

Expedia has 4 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, Stamford Town Hall and Clarksburg State Park 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.