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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Windham

Lounge
Bromley View Inn
Bromley View Inn
3.5 star property
9.0 out of 10, Wonderful, (395)
"Great place and close to everything "
United States
Debra
Bromley View Inn
Porch
Harvest Barn Inn
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (240)
"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "
United States
Suzanne
Harvest Barn Inn
Exclusive Room | Tempur-Pedic beds, individually furnished, free WiFi, bed sheets
Four Columns Inn
Four Columns Inn
3.0 star property
9.6 out of 10, Exceptional, (8)
"Lovely staff, amazing ambiance!"
United States
Julie
Four Columns Inn
Kayaking
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
2.5 star property
9.2 out of 10, Wonderful, (110)
"Lovely pleasant stay. "
United States
Heather
The price is AED 631
AED 694 total
includes taxes & fees
24 Oct - 25 Oct
Blue Gentian Lodge at Magic Mountain
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (335)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 579
AED 636 total
includes taxes & fees
3 Nov - 4 Nov
Colonel Williams Inn
Front of property
The Inn at Ormsby Hill
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, (143)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 657
AED 723 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Ormsby Hill
Exterior
Deerfield Valley Inn
Deerfield Valley Inn
3.0 star property
9.6 out of 10, Exceptional, (76)
"Very private, very quiet, pet friendly, great staff"
United States
Blendell
Deerfield Valley Inn
Property grounds
The Inn at Manchester
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (273)
"Beautiful area, great staff"
United States
Matthew
The price is AED 545
AED 600 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Manchester
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (102)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 737
AED 803 total
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery
Garden
Big Bears Lodge
Big Bears Lodge
3.0 star property
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 AED 612
AED 674 total
includes taxes & fees
27 Oct - 28 Oct
Big Bears Lodge
Standard Room, 1 King Bed, Mountain View | Mountain view
North Shire Lodge
North Shire Lodge
3.0 star property
9.4 out of 10, Exceptional, (155)
"Loved our stay at North Shire Lodge.."
United States
Mary
The price is AED 650
AED 716 total
includes taxes & fees
26 Oct - 27 Oct
North Shire Lodge
Mountain view
Windham Hill Inn
Windham Hill Inn
4.0 star property
8.4 out of 10, Very Good, (36)
"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 AED 666
AED 726 total
includes taxes & fees
28 Oct - 29 Oct
Windham Hill Inn
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!
Room in Historic Inn! 20 Minutes to Okemo!
9.2 out of 10, Wonderful, (17)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is AED 364
AED 613 total
includes taxes & fees
2 Nov - 3 Nov
Room in Historic Inn! 20 Minutes to Okemo!
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!
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 AED 327
AED 592 total
includes taxes & fees
2 Nov - 3 Nov
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
9.6 out of 10, Exceptional, (170)
"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 AED 856
AED 1,760 total
includes taxes & fees
26 Oct - 27 Oct
Hill Farm Inn
Exterior
Deerhill Inn
Deerhill Inn
3.5 star property
9.6 out of 10, Exceptional, (222)
"An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!"
United States
Clarence
The price is AED 685
AED 754 total
includes taxes & fees
9 Nov - 10 Nov
Deerhill Inn
Lobby
Chesterfield Inn
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
2 Nov - 3 Nov
Chesterfield Inn
Interior
King & Queen Suite in Historic Inn Circa 1780
King & Queen Suite in Historic Inn Circa 1780
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 AED 511
AED 835 total
includes taxes & fees
4 Nov - 5 Nov
King & Queen Suite in Historic Inn Circa 1780
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is AED 400
AED 654 total
includes taxes & fees
2 Nov - 3 Nov
Honeymoon Suite with Jacuzzi Tub in Historic 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.
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Top Windham Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"Beautiful property, wonderful views, loved our room, loved the huge indoor heated pool and the outdoor jacuzzi. Bar staff, food and drinks were fantastic at the on site bar/restaurant The Falcon, shout out to Maddie for being awesome. Bummer the steal house was closed the entirety of our stay (Sun-Weds), but what are ya gonna do. Would recommend, and would love to return next autumn. "
Mary 3-night trip
Posted 5 days ago
The Equinox Golf Resort & Spa

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 could be the perfect alternative for your vacation.
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: Big Bears Lodge: 24 rooms. 16.9 mi (27.1 km) from the heart of Windham. Enjoy the free cooked breakfast and outdoor pool. Deerfield Valley Inn: 9 rooms. 17.4 mi (28.1 km) from the downtown core. Enjoy the unique décor and fireplace in the lobby. Bromley View Inn: 16 rooms. Situated 10.5 mi (16.9 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 heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Four Columns Inn: 15 rooms. Located 13.3 mi (21.5 km) from the core of Windham.
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.