Windham Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Windham holiday rentals

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

Grafton

Eleanor D.

HK$2,905 total

includes taxes & fees

27 Aug - 28 Aug

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

Londonderry

Meghan R.

HK$4,732 total

includes taxes & fees

27 Aug - 28 Aug

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

Stratton

HK$2,033 total

includes taxes & fees

26 Aug - 27 Aug

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

Stratton

HK$1,777 total

includes taxes & fees

26 Aug - 27 Aug

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

Stratton

eric m.

HK$2,485 total

includes taxes & fees

26 Aug - 27 Aug

6. Cozy Bromley Retreat

Bromley Mountain

Jaime

HK$2,687 total

includes taxes & fees

26 Aug - 27 Aug

7. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Jamaica

Michael A.

HK$6,575 total

includes taxes & fees

1 Sept - 2 Sept

8. Long Trail House at Stratton Mountain Resort

Stratton

William

HK$3,060 total

includes taxes & fees

30 Aug - 31 Aug

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Top Windham Hotel Reviews

Pointe at Castle Hill Resort

10/10 Excellent

"First stayed at the Pointe in 2023 and it was an enjoyable stay. Returned this year and our stay did not disappoint. The pool and the hot tub were particularly enjoyable."

Hideaway Inn Mt. Snow

10/10 Excellent

"We will definitely return to the Hideaway! We got a text before arrival with our room number and code which was very convenient. The hotel is warm and cozy and beautifully decorated. There is neat stuff to look at everywhere. The 3 floors of common spaces were really cool with a lot to offer, like a water bottle filler and coffee maker. It could use to be cleaned a little more often. When we arrived, the playroom had toys all over the floor and there were sticky drink marks on the bar and crumbs on the coffee table. Someone had crushed the chalk under the dart board and all but 1 of the darts was broken. Regardless, we had a blast playing classic Mario on the arcade game. The living room upstairs was gorgeous, next time we will be sure to use that to play games and maybe watch a movie. We didn’t use the pool because it looked green (we opted to go to the lake instead) but we did make a fire and made s’mores down at one of the fire pits on our second night which was so nice to have. The closet in the hallway to grab towels and such is super convenient and the manager was only a text away if you needed anything. Our room was beautiful and so big. We loved the balcony and the record player in the room was a cool touch my boys had fun listening to. This is a very quiet property with a lot to keep families occupied or just relax and enjoy nature. We had a wonderful stay and when we met the manager she was so sweet! We absolutely loved it and will return for future VT trips."

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windham!

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, 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 Windham has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: This highly rated holiday home rental in Windham is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

With 11 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Magic Mountain Ski Resort and Jamaica State Park.

What’s a holiday rental in Windham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip.

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Check prices for these dates

Our top choices for Windham holiday rentals

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

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

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

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

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

6. Cozy Bromley Retreat

7. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

8. Long Trail House at Stratton Mountain Resort

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

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

11. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

12. Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

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

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

15. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

16. Charming Chester Farmhouse near Near VT Slopes

17. Long Trail House South Wing 2B2B Condo

18. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

19. 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.

20. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Find holiday rentals that suit your style

Top Windham Hotel Reviews

Pointe at Castle Hill Resort

Hampton Inn and Suites Manchester

The Palmer House Resort, an Ascend Collection Hotel

Bromley View Inn

Colonial Motel

Hampton Inn Brattleboro

Hideaway Inn Mt. Snow

Holiday Inn Express Hotel & Suites Brattleboro by IHG

The Equinox Golf Resort & Spa

Find out more about Windham

Frequently asked questions

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