Windham Vacation Rentals

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Vacation Rentals in Windham

Smart TV, fireplace, foosball, table tennis
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham
10.0 out of 10, Exceptional, (54)
"Consistently great time at this place (3rd time there)"
United States
Chad B.
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
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, (77)
"Nice, clean room in prime location"
United States
Kristin
$369 nightly
The price is $417
Nov 18 - Nov 19
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
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, (74)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$224 nightly
The price is $253
Nov 18 - Nov 19
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Fridge, microwave, oven, stovetop
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Sunderland
10.0 out of 10, Exceptional, (126)
"I stayed here with 8 people and the house was great for all of us. It was clean and comfortable and the hot tub was an extra plus. I would recommend staying here!"
United States
Alexa S.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
8.0 out of 10, Very Good, (41)
"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "
United States
John Q.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Cozy 2-bedroom cabin near Mount Snow 3 min drive

2.0 star property
Dover
9.6 out of 10, Exceptional, (9)
"Great cabin! Perfect for our family of 4 and our dog! Very close to mount snow and walking distance to great restaurants! "
United States
Lisa R.
Cozy 2-bedroom cabin near Mount Snow 3 min drive
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (11)
"Great place . Would highly recommend it.!"
United States
Peter G.
$312 nightly
The price is $339
Nov 18 - Nov 19
Total with taxes and fees
Owl's Nest Treehouse
3 bedrooms, internet, bed sheets
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Andover
9.0 out of 10, Wonderful, (29)
"The property was beautiful with a gorgeous view. The cleanliness of the house was less than expected. Cobwebs, stained bedspread, dirty cabinets, and handprints all over the loft windows gave the impression that it hadn't been thoroughly cleaned in a while. There were also several lightbulbs that were burned out on arrival. If it were cleaned up properly, it would be a great place to stay."
United States
Stephen T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
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, (166)
"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
$319 nightly
The price is $357
Nov 17 - Nov 18
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
9.8 out of 10, Exceptional, (127)
"Enjoyed our stay immensely"
United States
jim m.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend
10.0 out of 10, Exceptional, (5)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out

Seasons On Mount Snow - Ski-in/Ski-out

Dover
9.8 out of 10, Exceptional, (180)
"I would recommend this place. It was very enjoyable. Stay love the area and the staff at the swimming pool were very nice."
United States
Richard
Seasons On Mount Snow - Ski-in/Ski-out
Interior
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Manchester
10.0 out of 10, Exceptional, (58)
"Great place for a big group. Kids loved exploring and parents loved the space."
United States
John L.
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved
Property grounds
Long Trail House Studio at Stratton Mountain Resort

Long Trail House Studio at Stratton Mountain Resort

Stratton
10.0 out of 10, Exceptional, (64)
"Our stay was incredible. The location was perfect, room and facility was clean. Thank you for being a great host, 10/10!"
United States
Tyler M.
Long Trail House Studio at Stratton Mountain Resort
Exterior detail
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow
10.0 out of 10, Exceptional, (95)
"Our stay was great! Very nice cabin on the water with wood burning fireplace, fire pit, gas grill, and everything else you need for a pleasant get a way!"
United States
Jason B.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Outdoor dining
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mount Holly
9.8 out of 10, Exceptional, (225)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
United States
Derek G.
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
TV, fireplace
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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

Stratton
8.4 out of 10, Very Good, (26)
"Great location close to lift. Condo is clean and well appointed."
United States
Grace Ann B.
$246 nightly
The price is $278
Nov 18 - Nov 19
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

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

Jamaica
9.6 out of 10, Exceptional, (21)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
United States
Ross P.
$580 nightly
The price is $655
Nov 19 - Nov 20
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Dining
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Winhall
9.6 out of 10, Exceptional, (241)
"What a wonderful place to stay! My boyfriend and I too advantage of the beautiful deck and had coffee and dinner on it every day. We also used the charcoal grill to cook dinner and the wood stove outside, for a beautiful outside dining expereince! We would love to come back again!"
United States
Katherine B.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Ludlow
9.6 out of 10, Exceptional, (19)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
United States
Kristen R.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
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

Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Room was clean, spacious. The hotel was close to the outlets which was a plus. We liked the convenience of being provided with our room number and code to our room, which was helpful, as we didnt have to arrive at the hotel by a certain time to be able to check in."
Sarah 3-night trip
Posted 2 days ago
Aspen At Manchester

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $253 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 popular places like Stratton Mountain Resort and Mount Snow.

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.