Windham Vacation Rentals from ￥35,662: Search Short-Term Rentals

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Our top choices for Windham vacation rentals

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

1. Long Trail House at Stratton Mountain Resort

Stratton

Michael

￥69,756 total

includes taxes & fees

Oct 19 - Oct 20

A cabin with a sloped roof, surrounded by snow-covered trees, and illuminated by string lights.

2. Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont

Jamaica

￥192,874 total

includes taxes & fees

Nov 3 - Nov 4

A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

3. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Londonderry

Tim M.

￥193,535 total

includes taxes & fees

Nov 3 - Nov 4

A view through a window with a wooden frame, revealing a forested area with snow on the ground.

4. Cozy cabin in charming Londonderry

Londonderry

Eric H.

￥43,499 total

includes taxes & fees

Oct 28 - Oct 29

A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

5. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Londonderry

Marcel P.

￥133,812 total

includes taxes & fees

Oct 19 - Oct 20

A red house with a covered porch and a chimney.

6. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

￥58,604 total

includes taxes & fees

Oct 21 - Oct 22

7. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

Lorraine C.

￥111,895 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living room with a high ceiling, wooden beams, a large sofa, a dining table, and a view of the outdoors through large windows.

8. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

Jamaica

fran g.

￥164,488 total

includes taxes & fees

Oct 20 - Oct 21

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Top Windham Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

8/10 Good

"Our room was amply sized to fit our family, including our pack-n-play fro our toddler. The provided breakfast was great the three morning we were there. The indoor pool was cold during our stay, and appeared to be undergoing some renovation. Otherwise it was a great stay."

Aspen At Manchester

10/10 Excellent

"Great location, simple room--minimalist but nice with microwave, fridge. Was a great place to set up headquarters for our trip to Vermont. Beautiful view behind the motel with firepits. It is a self-serve kind of property, which suited us well. We stayed 4 days and they didn't come to clean throughout. But we could go to the office and pick up anything we needed: extra toiletries, towels, etc. We enjoyed staying at the Aspen."

Pointe at Castle Hill Resort

10/10 Excellent

"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."

Find out more about Windham

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Frequently asked questions

Are there vacation rentals in Windham?

Yes, we give you a choice of vacation rentals near the most popular points of interest in Windham, or you can select a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Windham has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: Visitors give good reviews to this Windham vacation home rental, which is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Windham?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What’s there to see and do in Windham?

Explore the area and family-friendly sights such as Vermont Country Store, or get out into nature at a spot like Lowell Lake State Park. In the larger area, you’ll find Magic Mountain Ski Resort and Jamaica State Park.

What’s a vacation rental in Windham like?

Vacation rentals are private properties where you can stay for several days or longer in Windham. Vacation rentals feature amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Windham vacation rentals

1. Long Trail House at Stratton Mountain Resort

2. Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont

3. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

4. Cozy cabin in charming Londonderry

5. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

6. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

7. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

8. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

9. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

10. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

11. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

12. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

13. Beautiful country cabin with hot tub and outdoor shower in Londonderry

14. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

15. Long Trail House South Wing 2B2B Condo

16. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

17. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

18. Lovely ski-in/out condo steps from ski lift with trails and amazing views

19. Tranquil Brookside Retreat with Hot Tub & Firepit

20. Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

Hampton Inn and Suites Manchester

Travelodge by Wyndham Brattleboro VT

Hideaway Inn Mt. Snow

The Manchester View

Jackson Gore Village, A Vail Resorts Property

Aspen At Manchester

Pointe at Castle Hill Resort

The Palmer House Resort, an Ascend Collection Hotel

Find out more about Windham

Frequently asked questions

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