Windham Holiday Rentals from AU$325: Search Short-Term Rentals

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Our top choices for Windham holiday 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

includes taxes & fees

21 Oct - 22 Oct

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

Jamaica

includes taxes & fees

18 Nov - 19 Nov

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.

includes taxes & fees

3 Nov - 4 Nov

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.

includes taxes & fees

29 Oct - 30 Oct

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.

includes taxes & fees

3 Nov - 4 Nov

A red house with a covered porch and a chimney.

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

Grafton

Eleanor D.

includes taxes & fees

22 Oct - 23 Oct

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

Andover

Lorraine C.

includes taxes & fees

21 Oct - 22 Oct

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.

includes taxes & fees

21 Oct - 22 Oct

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Top Windham Hotel Reviews

Pointe at Castle Hill Resort

8/10 Good

"The hotel was clean but older. Nothing special. Basic hotel room."

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"We stayed in room 74-it was beautiful and so clean! From the time we checked in till the time we left, everyone went out of their way to make us feel welcome! The breakfast was delicious! And the gentleman who checked us in was very kind. We would 100% stay there again!!!"

Hideaway Inn Mt. Snow

8/10 Good

"It was a tablet check in which was fairly easy but sends the room number and access code to your e mail address . The rooms were clean and tidy. Free hot drinks in an area on a lower floor. Check out didn’t work on the tablet, so used the telephone. Nobody answered that call, but a member of staff appeared and said everything was fine and we could leave. Diving distance to local restaurants and there were numerous. The gondola was close by, although we didn’t go to the top because it was raining hard and didn’t think we would see much."

The Putney Inn

10/10 Excellent

"Our room was quiet, clean and very comfortable. Breakfast was nice--more than enough for a decent breakfast before heading out-- waffle maker, toast, yogurt, cold cereal, fruit, juice coffee, and tea, etc. The grounds were beautiful and well kept. The staff was very helpful and parking was super easy right next to the room. The only slight downside was a strong musty odor in the entryway of the room (106), but the room itself smelled clean and was just fine."

Hampton Inn Brattleboro

10/10 Excellent

"Excellent place to stay, clean seems new, has small pool and water bath (kind of like jacuzzi) clean room, staff is nice and friendly. Includes breakfast and all day coffee or hot water to make teas (that is a must for me) as I need to make me teas few times a day. Would recommend for sure. If it was cheaper than it would really be off the charts but I will not include that into the review."

Find out more about Windham

Everything you need to know about Windham 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 Windham 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 Windham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Windham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham 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 Windham holiday rentals we have selected for you start as low as AU$325 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham 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 Windham 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 Windham 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 Windham. 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

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 10 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. 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 holiday rentals that suit your style

Top Windham Hotel Reviews

Pointe at Castle Hill Resort

Grand Summit Resort, A Vail Resorts Property

Hampton Inn and Suites Manchester

Colonial Motel

The Palmer House Resort, an Ascend Collection Hotel

Hideaway Inn Mt. Snow

The Putney Inn

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Find out more about Windham

Frequently asked questions

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