Windham Chalets from CA $589

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Our top choices for Windham chalets

A white, single-story cabin with a red door, surrounded by trees.

1. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

Jamaica

fran g.

CA $1,309 total

includes taxes & fees

Nov 3 - Nov 4

A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

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

Wardsboro

Jeff H.

CA $589 total

includes taxes & fees

Oct 27 - Oct 28

A wooden deck with a table and chairs, surrounded by a forest.

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

Wardsboro

Carly L.

CA $635 total

includes taxes & fees

Nov 9 - Nov 10

A small, single-story house with a front porch, a red door, and a white fence.

4. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

Wardsboro

Lisa B.

CA $657 total

includes taxes & fees

Oct 27 - Oct 28

A two-story house with a covered porch, surrounded by a well-maintained garden and trees.

5. Tranquil Brookside Retreat with Hot Tub & Firepit

Peru

Michael B.

CA $969 total

includes taxes & fees

Nov 1 - Nov 2

A wooden house with a porch lit by string lights, surrounded by snow.

6. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

CA $611 total

includes taxes & fees

Nov 9 - Nov 10

A two-story wooden cabin with a stone foundation, large windows, and a stone chimney.

7. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

Stratton

samantha b.

CA $1,021 total

includes taxes & fees

Oct 26 - Oct 27

A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

8. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

CA $625 total

includes taxes & fees

Oct 26 - Oct 27

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Top Windham Hotel Reviews

Aspen At Manchester

8/10 Good

"I loved having two bedrooms and two bathrooms all to ourselves. The only problem we had was the water pressure in one of the bathrooms. It was so low of a pressure my husband came out and went to the other one."

Brittany Motel

8/10 Good

"I liked the clean room and bathroom was reasonably clean. The only staff I encountered was the gentleman who spoke little English cleaning the rooms. The shared kitchen was quite fine, and I can see how dog owners would appreciate the more purposeful backyard dog run/ play area. My only strong complaint is the parking setup, which made it way too tight to park my car on the diagonal (between 2 vehicles that had better, more spacious perpendicular parking) in the corner for Room # 5 (I suspect that they book this room last, as it is the least convenient or assured comfortable assigned/ suggested parking space on the property. Arriving around 8 pm and finding that I could barely (mere inches on both sides) fit my standard RAV4 in this diagonal space was an unnerving / stressful way to arrive and unload. Once I brought in my belongings, I parked further down the line so as to lessen the chances of getting dinged in the morning by the other parked cars. Other than that, the bed was reasonably comfortable and I was happy with the price. Can’t say that I was impressed enough to necessarily stay loyal to this location, though."

The Equinox Golf Resort And Spa

8/10 Good

"The property is a beautiful old hotel, but you can tell they are having a hard time keeping it up. The rooms are big and cozy at the same time, the beds comfortable but the bathroom had some ventilation issues and therefore was a little moldy. While the pool was great, it was a shame the sauna was not working. All in all a nice stay though."

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"We stayed in room 74-it was beautiful and so clean! From the time we checked in till the time we left, everyone went out of their way to make us feel welcome! The breakfast was delicious! And the gentleman who checked us in was very kind. We would 100% stay there again!!!"

Find out more about Windham

Windham Chalets information

Number of reviews	112
Accommodation	94 Chalets
Lowest Price	CA $589
Highest Price	CA $1,309

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham chalets

1. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

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

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

4. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

5. Tranquil Brookside Retreat with Hot Tub & Firepit

6. Chalet Mount Snow/Stratton Skiing/hiking

7. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

8. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

9. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

10. NEW Private Chalet - 4 mins to Mt Snow

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Aspen At Manchester

Hampton Inn and Suites Manchester

The Putney Inn

Brittany Motel

The Equinox Golf Resort And Spa

Hampton Inn Brattleboro

Kimpton Taconic Hotel by IHG

Colonial Motel

The Palmer House Resort, an Ascend Collection Hotel

Find out more about Windham

Windham Chalets information

Explore a world of travel with Expedia

Search Chalets in Windham from CA $589

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham chalets

1. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

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

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

4. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

5. Tranquil Brookside Retreat with Hot Tub & Firepit

6. Chalet Mount Snow/Stratton Skiing/hiking

7. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

8. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

9. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

10. NEW Private Chalet - 4 mins to Mt Snow

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Aspen At Manchester

Find out more about Windham

Windham Chalets information

Explore a world of travel with Expedia