Windham County Holiday Rentals from AU$444: Search Short-Term Rentals

A wooden covered bridge over a river with stone walls on either side.

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Our top choices for Windham County holiday rentals

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

Dover

Tania J.

includes taxes & fees

9 July - 10 July

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

includes taxes & fees

14 July - 15 July

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Roy-michael G.

includes taxes & fees

9 July - 10 July

Smart TV, fireplace, Netflix, streaming services

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

includes taxes & fees

13 July - 14 July

The MountainTop - Stratton & Mt Snow - Fire Pit

Stratton

Brenna G.

includes taxes & fees

9 July - 10 July

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Susan S.

includes taxes & fees

21 July - 22 July

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Wardsboro

Jeff H.

includes taxes & fees

22 July - 23 July

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

Brattleboro

James M.

includes taxes & fees

20 July - 21 July

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Top Windham County Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"It was a quiet, clean room. Nice one-night stopover. Everyone was kind and helpful."

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good

"We were pleasantly surprised to find a refrigerator and coffee maker in our room! Last year when we stayed here we did not have either (check ahead if these are important to you). The location is perfect for spending time at Stratton Mountain Village. The staff were friendly and helpful. The hotel is dated and in need of upgrades, but has everything you need!"

Vikings Villages Resort

10/10 Excellent

"We had an amazing stay at Viking Village resort! It is an absolute hidden gem and truly felt like a fairytale escape. The cozy wooden houses are free-standing, which gives you excellent privacy, making them perfect for either a family trip or a solo getaway. I was so pleasantly surprised to find a fully equipped kitchen inside. The entire area is incredibly quiet with absolutely no outside noise—just total peace. On the premises, they have a great fireplace setup and the most amazing, cute goats! My only regret is that we only stayed for one night. We are already hoping to come back for a longer stay next time. It is absolutely worth the drive!"

Latchis Hotel

10/10 Excellent

"I love this place. It's really special. Some people to preserve what was special and exciting and authentic about a historic space and these are my people. They have the amenities you need (great bed and linens, refridgerator, microwave, good towels). They have the amenities you don't need but love! (record players in all rooms and throughout the hotel and vintage vinyl readily available, cucumber water in the lobby, a coffe and tea station in the lobby, a postcard writing station, easy access to a movie theater). This won't be everybodies cup of tea. What used to be luxury amenities are preserved a curiousities, the halls feel like a dorm, and brattleboro is on a downturn. But Brattleboro is also really beauitful, with some lovely restaurants and arts venues. And I love everything about it. If you stay - make sure to stay see a movie. It's gorgeous in there. Turkish breakfast at Tulip in amazing. Shim La's really good. check out the river. Stone Church is a fun venue. And Ther'es a lot to see and love in brattleboro. Also Go to chesterfield and check out madame sherri's castle and the gorge. Enjoy!"

The Covered Bridge Inn

8/10 Good

"Well, it definitely is a motel. We drove in and immediately saw shopping carts in a pile in the corner of the parking lot. There was shrubbery all over. Cracks in the parking lot. The lobby isn't clearly marked and you have to drive toward the back of the parking lot before you see it (side entrance). The staff wasn't out front so you had to hit a doorbell. They answer and tell you to take your key card from a "lockbox" which is open and your key cards are sitting there out in the open. They said "okay, you're good" without checking ID or credit card. There weren't great markings where to go to find the room. The hallways smelled like a mix of old cigarettes, weed, and incense. The room did seem pretty clean despite all of that. I could tell they took care of the rooms. There was a hidden hole in the room of the floor underneath the carpet, though, that would have been easy to trip over. All said, I still got a decent night sleep but probably wouldn't stay there again."

Find out more about Windham County

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$444 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.

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Windham County holiday rentals

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Chalet Mount Snow/Stratton Skiing/hiking

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

The MountainTop - Stratton & Mt Snow - Fire Pit

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

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

Stunning Glass House nestled in the Vermont wilderness!

Long Trail House at Stratton Mountain Resort

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

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

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Family Friendly Hilltop House In Putney Vermont

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Mt Snow Game Room Chalet with Hot Tub

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Vikings Villages Resort - Double Bed Room

Find holiday rentals that suit your style

Top Windham County Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

The Black Bear Lodge at Stratton Mountain Resort

Vikings Villages Resort

Colonial Motel

Latchis Hotel

Hampton Inn Brattleboro

The Covered Bridge Inn

Blue Gentian Lodge at Magic Mountain

Grand Summit Resort, A Vail Resorts Property

Find out more about Windham County