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Check prices for these dates

Our top choices for Windham holiday rentals

1. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is £199
includes taxes & fees
19 Nov - 20 Nov
Cozy cabin in charming Londonderry

2. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is £193
includes taxes & fees
18 Nov - 19 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (175 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
The price is £267
includes taxes & fees
9 Nov - 10 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

4. Fourth-floor Stratton Village studio with valley-view balcony

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is £171
includes taxes & fees
18 Nov - 19 Nov
Fourth-floor Stratton Village studio with valley-view balcony

5. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (37 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is £233
includes taxes & fees
13 Nov - 14 Nov
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

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

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
The price is £260
includes taxes & fees
19 Nov - 20 Nov
Beautiful country cabin with hot tub and outdoor shower in Londonderry

7. Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.0 out of 10, Wonderful, (7 reviews)
"Beautiful location and place. Could have been a bit cleaner (windows, TV, shower curtain) and the hot tub worked well but definitely needed to be cleaner."
United States
Tracey V.
The price is £458
includes taxes & fees
9 Nov - 10 Nov
Romantic Riverbed Treehouse - hot tub & new sauna!

8. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
The price is £328
includes taxes & fees
8 Nov - 9 Nov
Long Trail House at Stratton Mountain Resort

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

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (25 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is £414
includes taxes & fees
8 Nov - 9 Nov
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

10. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is £192
includes taxes & fees
8 Nov - 9 Nov
Cozy Village Condo-Okemo Shuttle

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

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is £506
includes taxes & fees
11 Nov - 12 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

12. Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"The place was clean and had all the essentials. Right across from pool and great stay."
United States
Andrew P.
The price is £312
includes taxes & fees
29 Nov - 30 Nov
Cozy Bromley Retreat — Ski-In, Ski-Out

13. Founders Lodge condo at Stratton Mountain with gas fireplace

Founders Lodge condo at Stratton Mountain with gas fireplace
Stratton
8.0 out of 10, Very good, (1 review)
The price is £302
includes taxes & fees
10 Nov - 11 Nov
Founders Lodge condo at Stratton Mountain with gas fireplace

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

Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
The price is £779
includes taxes & fees
9 Nov - 10 Nov
Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

15. Condo a short walk to the Sachem trail with seasonal pool and tennis

Condo a short walk to the Sachem trail with seasonal pool and tennis
Ludlow
The price is £210
includes taxes & fees
11 Nov - 12 Nov
Condo a short walk to the Sachem trail with seasonal pool and tennis

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

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (37 reviews)
"Excellent place! Impeccable!"
United States
Susan F.
The price is £391
includes taxes & fees
10 Nov - 11 Nov
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

17. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is £192
includes taxes & fees
15 Nov - 16 Nov
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

18. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is £169
includes taxes & fees
15 Nov - 16 Nov
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

19. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (8 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
Long Trail House South Wing 2B2B Condo

20. Insanely romantic treehouse perched next to a stream and rolling hills.

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is £636
includes taxes & fees
11 Nov - 12 Nov
Insanely romantic treehouse perched next to a stream and rolling hills.
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.

Find holiday rentals that suit your style

Top Windham Hotel Reviews

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, apart-hotels, 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 favorite 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 depends 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 £168 per night. Entering your travel dates in the search wizard you might find 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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