Windham Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Windham holiday rentals

Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (20 reviews)
"Amazing place, cozy, clean and organized. I loved it and I want to come back again."
United States
Alex F.
The price is HK$2,150
HK$2,553 total
includes taxes & fees
15 Apr - 16 Apr
Owl's Nest Treehouse
Exterior

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, (168 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is HK$1,329
HK$2,714 total
includes taxes & fees
8 Apr - 9 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is HK$1,055
HK$1,961 total
includes taxes & fees
14 Apr - 15 Apr
Wellness Getaway with a Personal Sauna, and Private River Beach!
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (17 reviews)
"It was an amazing experience! "
United States
Gruha
The price is HK$1,368
HK$2,425 total
includes taxes & fees
19 Apr - 20 Apr
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,523
HK$1,873 total
includes taxes & fees
29 Mar - 30 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,291
HK$2,410 total
includes taxes & fees
29 Mar - 30 Mar
Family Friendly Hilltop House In Putney Vermont
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (51 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,254
HK$4,653 total
includes taxes & fees
30 Mar - 31 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior

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 HK$1,161
HK$2,770 total
includes taxes & fees
8 Apr - 9 Apr
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Outdoor pool, a heated pool

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

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is HK$449
HK$2,452 total
includes taxes & fees
29 Mar - 30 Mar
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is HK$1,032
HK$2,066 total
includes taxes & fees
8 Apr - 9 Apr
The Studio with a View. Bring your dog, too!
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is HK$665
HK$1,609 total
includes taxes & fees
31 Mar - 1 Apr
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (78 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$618
HK$2,049 total
includes taxes & fees
9 Apr - 10 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is HK$446
HK$2,317 total
includes taxes & fees
9 Apr - 10 Apr
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Children’s area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (10 reviews)
"Great location, steps to the Plaza trail, clean and well stocked with kitchen gear, towels etc. The furniture is a little dated but overall a great place to stay! Loved it!"
United States
Barb C.
The price is HK$709
HK$2,533 total
includes taxes & fees
29 Mar - 30 Mar
Cozy Bromley Retreat
Property grounds

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

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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 HK$438
HK$1,819 total
includes taxes & fees
8 Apr - 9 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is HK$1,197
HK$4,081 total
includes taxes & fees
28 Mar - 29 Mar
Outdoor Adventure Hub! Family Home in West Dover
Outdoor dining

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Clock Tower Base Area
8.6 out of 10, Excellent, (14 reviews)
"Great stay at Okemo. Super convenient to get to the lifts and unit was well maintained. Couldn’t find pillow cases for the pull out couch but otherwise everything was well appointed. Check in/check out was super easy. Thank you!"
United States
Kristin S.
The price is HK$829
HK$2,373 total
includes taxes & fees
30 Mar - 31 Mar
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
The price is HK$1,072
HK$3,326 total
includes taxes & fees
7 Apr - 8 Apr
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Exterior

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
The price is HK$1,472
HK$5,015 total
includes taxes & fees
1 Apr - 2 Apr
Romantic Riverbed Treehouse - hot tub & new sauna!
Beach

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (51 reviews)
"Two miles, four minutes from the slopes, very clean, well supplied and functional. "
United States
Simon V.
The price is HK$704
HK$2,253 total
includes taxes & fees
7 Apr - 8 Apr
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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 Windham Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Parking was available and easy, and it felt safe. Breakfast was slightly limited (boiled eggs, for example, would be a welcome breakfast item to enjoy with toast and the good coffee), but the fresh waffle was delicious, as well as the fruit and yogurt. The room was spotless, and the manager and his personnel excellent. "
Daniela 2-night trip
Posted 2 hours ago
The Putney Inn

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:

  • View our selection of featured holiday rentals in Windham
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

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 12 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.