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Stamford Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Stamford holiday rentals

A two-story blue house with a porch, surrounded by a garden with orange flowers.

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 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
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,782 reviews)
"We had an amazing stay."
United States
Luke
The price is NZ$177
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A kitchen with white cabinets, a wooden dining table, and pendant lights.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is NZ$825
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

4. Greylock Cabin

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 NZ$796
includes taxes & fees
22 Nov - 23 Nov
Greylock Cabin
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

5. 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 NZ$335
includes taxes & fees
29 Oct - 30 Oct
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

6. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is NZ$521
includes taxes & fees
25 Oct - 26 Oct
Downtown | Waterfront | Walk to Shops
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

7. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 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 NZ$527
includes taxes & fees
29 Oct - 30 Oct
2-Bdr Apt In Town, By the Water
A two-story house with a porch, surrounded by trees and snow.

8. 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
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

9. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is NZ$357
includes taxes & fees
26 Oct - 27 Oct
Cozy Home in Pownal VT
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

10. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (20 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is NZ$469
includes taxes & fees
29 Oct - 30 Oct
New Studio In Town, By the Water
A log cabin with a balcony, surrounded by trees.

11. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,047
includes taxes & fees
28 Oct - 29 Oct
Bear Creek Cabin
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

12. 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 NZ$1,049
includes taxes & fees
26 Oct - 27 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

13. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (18 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 NZ$489
includes taxes & fees
29 Oct - 30 Oct
Penthouse Apartment on Park Street
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

14. 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
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is NZ$661
includes taxes & fees
27 Oct - 28 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

15. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (117 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is NZ$670
includes taxes & fees
24 Oct - 25 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

16. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (9 reviews)
"A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing."
United States
Nicole H.
The price is NZ$1,352
includes taxes & fees
3 Nov - 4 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Maple live edge peninsula countertop by Vermont Live Edge just down the road!

17. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is NZ$989
includes taxes & fees
25 Oct - 26 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

18. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is NZ$2,230
includes taxes & fees
27 Oct - 28 Oct
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
An aerial view of a house surrounded by a forest with autumn foliage.

19. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is NZ$867
includes taxes & fees
27 Oct - 28 Oct
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

20. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.8 out of 10, Excellent, (6 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is NZ$1,096
includes taxes & fees
26 Oct - 27 Oct
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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

8/10 Good
"Very easy check in. Clean and safe."
James Kevin 3-night trip
Posted less than an hour ago
Vacation Village in the Berkshires

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, 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 NZ$177 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?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This holiday home rental outside of Stamford is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Buzzy Park, 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.