Search Bed and Breakfasts 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
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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, (290 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is ₹16,340
₹17,647 total
includes taxes & fees
22 Nov - 23 Nov
Albergo Allegria Hotel
A two-story house with a wrap-around porch, a steeply pitched roof, 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 ₹12,696
₹13,711 total
includes taxes & fees
16 Nov - 17 Nov
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, (307 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is ₹15,645
₹16,897 total
includes taxes & fees
15 Nov - 16 Nov
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, (335 reviews)
"Beautiful Inn. Every detail was so well thought out!"
United States
Nancy Joan
The price is ₹13,373
₹14,978 total
includes taxes & fees
15 Nov - 16 Nov
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, (307 reviews)
"Delicious breakfast and host was very knowledgeable about local things to do"
United States
Catherine
The price is ₹11,481
₹14,979 total
includes taxes & fees
22 Nov - 23 Nov
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, (234 reviews)
"Loved it"
United States
Glenn
The price is ₹11,616
₹13,721 total
includes taxes & fees
15 Nov - 16 Nov
Margaretville Mtn Inn B&B and Village Suites
A serene garden with a stone pathway, a small bridge, and a bench.

7. 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, (171 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 ₹18,755
₹21,006 total
includes taxes & fees
30 Nov - 1 Dec
Morning Glory B n B Woodstock NY
A large, white, two-story building with a symmetrical facade, central entrance, and columns.

8. 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, (89 reviews)
"The beauty and unique history of the property"
United States
Robin
The price is ₹22,363
₹24,600 total
includes taxes & fees
22 Nov - 23 Nov
The Queen of the Catskills B&B
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 ₹14,986
₹16,484 total
includes taxes & fees
19 Nov - 20 Nov
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

Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

See all hotels in Windham
Two skiers on a snowy slope with a valley and mountains in the background.

Top reviews in Windham

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

Albergo Allegria Hotel

Albergo Allegria Hotel
Windham

10/10 Excellent

Lovely hotel and a friendly welcome by the owners. Some small issues arose which we were not affected by, but we were always kept informed. Sadly, we couldn't enjoy the breakfast due to a bereavement in the family but am looking forward to it on our next visit. Thank you and here's hoping to come back soon.
United Kingdom
Michele
Reviewed January 29, 2026
Albergo Allegria Hotel

Frequently Asked Questions

Searching for B&Bs in Windham?

If you're interested in something a little different than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. If you're interested in playing some golf on your trip, Windham Country Club is a good spot to get in a game.

Why should you consider B&Bs instead of traditional hotels?

Every B&B has its own unique feel — whether it’s a garden for guests to admire or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a home away from home.

What are the best B&Bs in Windham?

Why not look at these B&Bs in Windham: Albergo Allegria Hotel: 21 rooms. Enjoy the unique decor and library. Antique Rose Inn Windham: 3 rooms. Enjoy the free full breakfast and unique decor.

When should I stay at a B&B in Windham?

When you're planning your trip to Windham, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

What is there to do in Windham?

Travellers enjoy Windham for its mountain views and coffee shops. If you're looking for some activities to entertain you on your trip, consider visiting Windham Country Club and Windham Vineyards and Winery. You should 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) away. If you'd like to venture out around the area, consider renting a car to explore more sights.