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

Find Chalets in Windham County, VT from $341

Compare and save

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Top Cities in Windham County

A rural landscape with rolling hills, a winding road, and autumn-colored trees.
ChaletsChalets

Whitingham

Whitingham

Our top choices for Windham County chalets

Exterior

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (289 reviews)
"Excellent stay, looking forward to visiting again!"
United States
Jordyn C
$162 nightly
The price is $179
Jul 21 - Jul 22
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property
Deluxe Chalet | Terrace/patio

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (207 reviews)
"It was very unique and great"
United States
Christopher
$184 nightly
The price is $201
Aug 3 - Aug 4
Total with taxes and fees
Vikings Villages Resort
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (925 reviews)
"Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!"
United States
Sharon
$125 nightly
The price is $137
Jul 12 - Jul 13
Total with taxes and fees
Latchis Hotel
Property grounds

Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
5.4 out of 10, (13 reviews)
"The bed was hard to sleep on, the outdoor pool was filled with dirt, the indoor pool/spa/massage area is dilapidated, and the continental breakfast offered the bare minimum. When using the shower, switching from tub to shower was a task in itself while the water pressure was weak"
United States
Paul
$77 nightly
The price is $84
Aug 2 - Aug 3
Total with taxes and fees
Colonial Motel
Exterior

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,006 reviews)
"A little overpriced but a good stay"
United States
David
$122 nightly
The price is $134
Jul 19 - Jul 20
Total with taxes and fees
Hampton Inn Brattleboro
Hiking

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.6 out of 10, Excellent, (117 reviews)
"Newly renovated, clean, easy self check in, and great location!"
United States
Dana
$119 nightly
The price is $131
Jul 19 - Jul 20
Total with taxes and fees
Hideaway Inn Mt. Snow
Exterior

Inn At Mount Snow

Inn At Mount Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (73 reviews)
"Staff was very attentive and friendly. Breakfast, continental, was good. The room was spectacular!"
United States
Susan
$118 nightly
The price is $130
Jul 22 - Jul 23
Total with taxes and fees
Inn At Mount Snow
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,003 reviews)
"Perfect for an overnight!"
United States
Lori
$127 nightly
The price is $139
Jul 22 - Jul 23
Total with taxes and fees
The Putney Inn
Exterior

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (832 reviews)
"Perfectly comfortable and convenient for us, and the complimentary breakfast buffet was better than most!"
United States
Bonnie
$126 nightly
The price is $139
Aug 9 - Aug 10
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Exterior

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.0 out of 10, Wonderful, (339 reviews)
"The hotel was beautiful and the staff was amazing!"
United States
kathleen
$269 nightly
The price is $296
Jul 12 - Jul 13
Total with taxes and fees
The White House Inn
Porch

Valley Craft Ales

Valley Craft Ales
2.0 star property
Wilmington
8.4 out of 10, Very Good, (228 reviews)
"Great location, lot of restaurants in a walking distance from the place."
United States
Gustavo
$142 nightly
The price is $156
Jul 10 - Jul 11
Total with taxes and fees
Valley Craft Ales
Exterior

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (655 reviews)
"Quiet and clean place to stay the night"
United States
Aigul
$84 nightly
The price is $93
Aug 9 - Aug 10
Total with taxes and fees
Econo Lodge Brattleboro South
Front of property - evening/night

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.4 out of 10, Good, (1,004 reviews)
"Clean room, useful fridge and microwave, safe parking."
United States
Elizabeth
$123 nightly
The price is $136
Aug 7 - Aug 8
Total with taxes and fees
The Covered Bridge Inn
Double Room | Terrace/patio

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (132 reviews)
"Staff very helpful. Everything was very clean"
United States
Patrick
$131 nightly
The price is $144
Jul 29 - Jul 30
Total with taxes and fees
Chalet 239
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (497 reviews)
"Bed was comfy. Room was clean. "
United States
Katherine
$135 nightly
The price is $149
Jul 12 - Jul 13
Total with taxes and fees
Black Mountain Inn
Reception

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (1,000 reviews)
"Amazing hotel"
United States
Luis
$140 nightly
The price is $154
Jul 30 - Jul 31
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Exterior

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (782 reviews)
"Good value!"
United States
Brian
$80 nightly
The price is $88
Jul 12 - Jul 13
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT
Exterior

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1,000 reviews)
"Breakfast was delicious!"
United States
Jean
$130 nightly
The price is $143
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (124 reviews)
"We had a wonderful stay! Great location and very friendly inn keeper. Would definitely stay again."
United States
Andrea
$121 nightly
The price is $133
Jul 26 - Jul 27
Total with taxes and fees
Deerfield Valley Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (46 reviews)
"The hot tub was so amazing"
United States
Mark
$204 nightly
The price is $222
Jul 15 - Jul 16
Total with taxes and fees
Four Columns Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham County Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"I think all Hilton hotels have the same small and flat pillows which are not comfortable to sleep on but over all, It was okay. May be I just need to change my option in choosing where to stay. Breakfast is the same."
Jocelyn 1-night trip
Posted 1 hour ago
Hampton Inn Brattleboro

Find out more about Windham County

Windham County Chalets information

Number of reviews
353
Accommodation
82 Chalets
Lowest Price
$341
Highest Price
$536

Explore a world of travel with Expedia