Windham County Holiday Rentals from AU$425: 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

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

Dover

Tania J.

includes taxes & fees

23 Aug - 24 Aug

2. Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Susan S.

includes taxes & fees

1 Sept - 2 Sept

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

Dover

Evan C.

includes taxes & fees

18 Sept - 19 Sept

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

Brattleboro

s p.

includes taxes & fees

6 Sept - 7 Sept

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

Grafton

Eleanor D.

includes taxes & fees

25 Aug - 26 Aug

Smart TV, fireplace, Netflix, streaming services

6. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

includes taxes & fees

9 Sept - 10 Sept

7. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Roy-michael G.

includes taxes & fees

26 Aug - 27 Aug

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

Stratton

eric m.

includes taxes & fees

25 Aug - 26 Aug

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Top Windham County Hotel Reviews

Latchis Hotel

8/10 Good

"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."

Deerfield Valley Inn

8/10 Good

"We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay."

Hideaway Inn Mt. Snow

10/10 Excellent

"We will definitely return to the Hideaway! We got a text before arrival with our room number and code which was very convenient. The hotel is warm and cozy and beautifully decorated. There is neat stuff to look at everywhere. The 3 floors of common spaces were really cool with a lot to offer, like a water bottle filler and coffee maker. It could use to be cleaned a little more often. When we arrived, the playroom had toys all over the floor and there were sticky drink marks on the bar and crumbs on the coffee table. Someone had crushed the chalk under the dart board and all but 1 of the darts was broken. Regardless, we had a blast playing classic Mario on the arcade game. The living room upstairs was gorgeous, next time we will be sure to use that to play games and maybe watch a movie. We didn’t use the pool because it looked green (we opted to go to the lake instead) but we did make a fire and made s’mores down at one of the fire pits on our second night which was so nice to have. The closet in the hallway to grab towels and such is super convenient and the manager was only a text away if you needed anything. Our room was beautiful and so big. We loved the balcony and the record player in the room was a cool touch my boys had fun listening to. This is a very quiet property with a lot to keep families occupied or just relax and enjoy nature. We had a wonderful stay and when we met the manager she was so sweet! We absolutely loved it and will return for future VT trips."

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$425 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

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

2. Cozy 3 bedroom condo 2.5 miles to Mount Snow

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

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

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

6. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

7. Chalet Mount Snow/Stratton Skiing/hiking

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

9. Family Friendly Hilltop House In Putney Vermont

10. Long Trail House at Stratton Mountain Resort

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

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

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

14. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

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

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

17. Stunning Glass House nestled in the Vermont wilderness!

18. A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

19. Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

20. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Find holiday rentals that suit your style

Top Windham County Hotel Reviews

Latchis Hotel

Hampton Inn Brattleboro

Black Mountain Inn

The Putney Inn

Inn At Mount Snow

Econo Lodge Brattleboro South

Travelodge by Wyndham Brattleboro VT

Deerfield Valley Inn

Hideaway Inn Mt. Snow

Find out more about Windham County

Windham County Holiday Rentals

Change your mind

Treat yourself

Be picky

Our top choices for Windham County holiday rentals

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

2. Cozy 3 bedroom condo 2.5 miles to Mount Snow

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

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

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

6. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

7. Chalet Mount Snow/Stratton Skiing/hiking

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

9. Family Friendly Hilltop House In Putney Vermont

10. Long Trail House at Stratton Mountain Resort

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

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

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

14. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

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

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

17. Stunning Glass House nestled in the Vermont wilderness!

18. A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

19. Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

20. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Find holiday rentals that suit your style

Top Windham County Hotel Reviews

Latchis Hotel

Find out more about Windham County

20. MtSnow* HotTub* Pool * AirHockeyPingPong Darts