A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Search B&B in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Windham bed & breakfast

A large, two-story house with multiple porches and string lights.

1. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (289 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is P10,943
P11,818 total
includes taxes & fees
Oct 21 - Oct 22
Albergo Allegria Hotel
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

2. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"A fantastic stay!"
United States
David
The price is P8,502
P9,182 total
includes taxes & fees
Oct 22 - Oct 23
Antique Rose Inn Windham
A park with Adirondack chairs and a table, surrounded by trees.

3. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (304 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is P10,455
P11,291 total
includes taxes & fees
Oct 22 - Oct 23
Mountain Treasure B&B
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

4. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (327 reviews)
"This property is exceptional from the food - bar - appointed room! I can't wait to visit again! The views -the service was impeccable! Thank you Katie and Jennifer(waitstaff) and owner Katie! You are all a WOW"
United States
Lianne
The price is P8,956
P10,031 total
includes taxes & fees
Oct 25 - Oct 26
Shandaken Inn
A large two-story house with a snow-covered roof and a front porch.

5. Meadowood Inn

Meadowood Inn
3.0 star property
Arkville
9.6 out of 10, Exceptional, (304 reviews)
"Delicious breakfast and host was very knowledgeable about local things to do"
United States
Catherine
The price is P7,689
P10,031 total
includes taxes & fees
Oct 26 - Oct 27
Meadowood Inn
A large, multi-story house with a snow-covered roof and a prominent tower.

6. Margaretville Mtn Inn B&B and Village Suites

Margaretville Mtn Inn B&B and Village Suites
3.0 star property
Margaretville
8.4 out of 10, Very good, (233 reviews)
"Loved it"
United States
Glenn
The price is P9,132
P10,675 total
includes taxes & fees
Nov 1 - Nov 2
Margaretville Mtn Inn B&B and Village Suites
A large, white, two-story building with a symmetrical facade, central entrance, and columns.

7. The Queen of the Catskills B&B

The Queen of the Catskills B&B
3.0 star property
Stamford
9.4 out of 10, Exceptional, (88 reviews)
"The beauty and unique history of the property"
United States
Robin
The price is P14,977
P16,474 total
includes taxes & fees
Nov 13 - Nov 14
The Queen of the Catskills B&B
A serene garden with a stone pathway, a small bridge, and a bench.

8. Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY
3.0 star property
Woodstock
8.6 out of 10, Excellent, (170 reviews)
"We had a great time! The host was super sweet and helpful, and the breakfast was delicious. Would stay again!"
United States
Lucian
The price is P13,793
P15,448 total
includes taxes & fees
Nov 2 - Nov 3
Morning Glory B n B Woodstock NY
A house with a porch and a sign that reads "Kroer Kun bed & breakfast".

9. River Run Bed and Breakfast

River Run Bed and Breakfast
3.0 star property
Fleischmanns
9.2 out of 10, Wonderful, (211 reviews)
"enjoyed our stay. breakfast was nice."
United States
Parag
The price is P10,014
P11,015 total
includes taxes & fees
Nov 10 - Nov 11
River Run Bed and Breakfast
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 Hotel Reviews

Red Ranch Motel

Red Ranch Motel

8/10 Good
"They need longer curtains to keep the bright lights outside from entering the room, otherwise it was a great stay. Very nice, clean and friendly place."
brynda 1-night trip
Posted 2 hours ago
Red Ranch Motel

Find out more about Windham

Windham B&B information

Number of reviews
1,661
Accommodation
16 B&B
Lowest Price
P9,182
Highest Price
P16,474

Frequently asked questions

Searching for B&Bs in Windham?
If you're looking for something a little different than your standard hotel, a stay at a bed and breakfast might be the perfect option for your trip. If you're interested in playing some golf on your trip, Windham Country Club is a good spot to tee off.
Why should you consider a B&B over a traditional hotel room?
Every B&B has a unique charm. Whether it's a picturesque garden or a beautiful breakfast room, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Windham?
Here are some B&Bs to check out in Windham: Albergo Allegria Hotel: 21 rooms. Enjoy the unique décor and library. Antique Rose Inn Windham: 3 rooms. Enjoy the free full breakfast and unique décor.
What's the best time of year to stay at a B&B in Windham?
When you're planning your trip 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 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Windham?
Travelers enjoy Windham for its mountain views and coffeehouses. If you're looking for some activities to entertain you on your trip, consider visiting Windham Country Club and Windham Vineyards and Winery. You might put Windham Mountain Resort and Catskill State Park on your list if you want to see more of the area.
How can I get to and around Windham?
Planning your excursions in and around Windham is easier with these transportation options. Fly into Hudson, NY (HCC-Columbia County), which is located 27.6 mi (44.4 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia