Windham County Holiday Rentals

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Top Holiday Rentals Destinations in Windham County

Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (68)
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is AU$572
includes taxes & fees
2 May - 3 May
Long Trail House at Stratton Mountain Resort
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is AU$549
includes taxes & fees
13 May - 14 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
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Oven, stovetop, dishwasher, coffee/tea maker
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is AU$520
includes taxes & fees
13 May - 14 May
VT Cabin overlooking the West River and Village
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Large property with multiple houses. Main house had plenty of room for our group of 14, and the guest house was a bonus area to hang out at night! The host was very responsive and easy to communicate with."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (37)
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
The price is AU$692
includes taxes & fees
13 May - 14 May
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Exterior
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
10.0 out of 10, Exceptional, (33)
"Great property. Spotless. Had everything we needed. Great information about the area. Bedroom configuration was perfect for us. Great ski on ski off location. Easy parking. Very responsive Host. Would definitely stay there again."
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
Interior
Lovely ski-in/out condo steps from ski lift with trails and amazing views
8.4 out of 10, Very good, (17)
"We had a great stay. It's not the most modern or squeaky clean condo, but honestly worked just fine. We were comfortable and enjoyed the fireplace. And you cannot beat the location to the slopes for the price. We will be staying here again."
The price is AU$508
includes taxes & fees
2 May - 3 May
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. The house has everything you need!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Fridge, microwave, oven, stovetop
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very good, (19)
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (39)
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is AU$514
includes taxes & fees
7 May - 8 May
Family Friendly Hilltop House In Putney Vermont
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (148)
"Carl was super nice, proactive, and a great communicator for this trip. The place was convenient, clean, in great repair, with lots of amenities and super easy to ski out. Little touches like a box of firewood, tinder, and matches and clear instructions on everything make things so pleasant. Would totally stay again. "
Seasons On Mount Snow - Ski-in/Ski-out
TV, fireplace
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (40)
"Can't beat the location. We had a great stay."
The price is AU$442
includes taxes & fees
2 May - 3 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
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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.

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

Windham County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham County. 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 County 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 County holiday rentals we have chosen for you start as low as AU$442 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Windham County rentals

At Expedia, we put the best Windham County 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 County 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 County 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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews in Windham County
Expedia verified reviews

The Covered Bridge Inn

The Covered Bridge Inn

5/5 Excellent
"This is a cheap hotel that is out of date but the room was spotless, no odors in room or bed! Very comfortable beds. Breakfast was basic but great bagels and real orange juice! The bat/shower looked brand new. Orbitz description said hotel was staffed until 11:00 pm but I called them to let them know we would be coming later and was told they are only there until 9:00 pm. They had a secure system for getting our key and it was easy snd flawless. Would def stay here again when needing a cheap clean room for the night. Also liked that Dunkin, Wendy’s and McDonalds are next door. "
A verified traveller stayed at The Covered Bridge Inn
Posted 1 day ago
The Covered Bridge Inn