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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Windham

Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (401)
"Overall a decent stay."
United States
Libin
Bromley View Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is SAR 544
SAR 598 total
includes taxes & fees
2 Dec - 3 Dec
Colonel Williams Inn
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
The price is SAR 541
SAR 698 total
includes taxes & fees
8 Dec - 9 Dec
Deerfield Valley Inn
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is SAR 724
SAR 797 total
includes taxes & fees
3 Dec - 4 Dec
The Inn at Ormsby Hill
Property grounds
The Inn at Manchester

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (280)
"Great establishment "
United States
Brenda
The price is SAR 619
SAR 681 total
includes taxes & fees
4 Dec - 5 Dec
The Inn at Manchester
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is SAR 697
SAR 760 total
includes taxes & fees
15 Dec - 16 Dec
Stone Hearth Inn and Eatery
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is SAR 450
SAR 723 total
includes taxes & fees
2 Dec - 3 Dec
Room in Historic Inn! 20 Minutes to Okemo!
Garden
Big Bears Lodge

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is SAR 626
SAR 688 total
includes taxes & fees
2 Dec - 3 Dec
Big Bears Lodge
Mountain view
Windham Hill Inn

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
United States
Brandon
The price is SAR 667
SAR 727 total
includes taxes & fees
10 Dec - 11 Dec
Windham Hill Inn
Property grounds
Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont

Manchester
10.0 out of 10, Exceptional, (1)
"Very nice and relaxing location"
United States
Jennifer C.
The price is SAR 295
SAR 513 total
includes taxes & fees
2 Dec - 3 Dec
Zen 10, relax and retreat in the heart of Vermont
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Chester Depot
9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
United States
Jacque
The price is SAR 446
SAR 740 total
includes taxes & fees
2 Dec - 3 Dec
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Front of property
Hill Farm Inn

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (173)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
The price is SAR 773
SAR 1,687 total
includes taxes & fees
14 Dec - 15 Dec
Hill Farm Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is SAR 1,130
SAR 1,226 total
includes taxes & fees
3 Dec - 4 Dec
Chesterfield Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is SAR 984
SAR 1,073 total
includes taxes & fees
2 Dec - 3 Dec
Echo Lake Inn
Exterior
Deerhill Inn

Deerhill Inn

3.5 star property
West Dover
9.6 out of 10, Exceptional, (224)
"Our hosts Arianne and Scott were very welcoming! The room was very comfortable and the breakfast and our server Cindy were amazing! Definitely recommend Deerhill Inn! "
United States
David
The price is SAR 746
SAR 821 total
includes taxes & fees
21 Dec - 22 Dec
Deerhill Inn
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is SAR 897
SAR 1,282 total
includes taxes & fees
2 Dec - 3 Dec
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Property grounds
Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Manchester
The price is SAR 295
SAR 513 total
includes taxes & fees
2 Dec - 3 Dec
Room 7 - family room sleeps 4
TV
Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat

Manchester
The price is SAR 295
SAR 513 total
includes taxes & fees
2 Dec - 3 Dec
Alpine 5, cozy Vermont retreat
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is SAR 1,047
SAR 1,525 total
includes taxes & fees
2 Dec - 3 Dec
King & Queen Suite in Historic Inn Circa 1780
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.
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Top Windham Hotel Reviews

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good. "
William 2-night trip
Posted 1 day ago
Jackson Gore Village

Frequently asked questions

Searching for B&Bs in Windham?
If you're looking for something a little more offbeat than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some top attractions, Stratton Mountain Resort and Mount Snow are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to mingle with other guests, and of course a scrumptious breakfast, B&Bs all have a unique setting.
What are the best B&Bs in Windham?
Below are some well-liked B&Bs in the area: Deerfield Valley Inn: 9 rooms. 17.4 mi (28.1 km) from the heart of Windham. Enjoy the unique décor and fireplace in the lobby. The Inn at Manchester: 18 rooms. 17.4 mi (28 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Four Columns Inn: 15 rooms. Situated 13.3 mi (21.5 km) from the heart of Windham. Enjoy the unique décor and coffee shop. Bromley View Inn: 16 rooms. 10.5 mi (16.9 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby. The Inn at Ormsby Hill: 10 rooms. Located 18.6 mi (29.9 km) from the core of Windham. Enjoy the free full breakfast and designer toiletries.
What's the best time of year to stay at a B&B in Windham?
When you're dreaming of a getaway to Windham, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 24°F. The snowiest months in Windham are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
How can I get to and around Windham?
You can map out your trip in and around Windham ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 15.5 mi (24.9 km) from the city center. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 26.9 mi (43.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.