Find Windham Bed And Breakfast

  • 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
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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 ￥27,536
￥29,739 total
includes taxes & fees
Nov 9 - Nov 10
Albergo Allegria Hotel
A mountain with dense green vegetation under a clear blue sky.

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 ￥21,395
￥23,107 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥26,308
￥28,413 total
includes taxes & fees
Nov 15 - Nov 16
Mountain Treasure B&B
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

4. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (334 reviews)
"Beautiful Inn. Every detail was so well thought out!"
United States
Nancy Joan
The price is ￥22,536
￥25,241 total
includes taxes & fees
Nov 9 - Nov 10
Shandaken Inn
A wooden deck with outdoor furniture, a barbecue grill, and a large planter with flowers.

5. Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.

Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.
Maplecrest
10.0 out of 10, Exceptional, (2 reviews)
"Agnes was an amazing host! Our stay was incredibly smooth and convenient. The drive to Hunter Mountain was just a short 15 minutes, making it so easy to get there. Breakfast was absolutely delicious, and it was a special touch knowing the eggs were from their own farmed chickens. When it was time to check out, they went above and beyond by helping us clear the snow off our car! We had such a great experience and will definitely be coming back for another visit!"
United States
Tiffany J.
The price is ￥22,029
￥25,845 total
includes taxes & fees
Nov 15 - Nov 16
Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.
A large two-story house with a snow-covered roof and a front porch.

6. Meadowood Inn

Meadowood Inn
3.0 star property
Arkville
9.6 out of 10, Exceptional, (306 reviews)
"Delicious breakfast and host was very knowledgeable about local things to do"
United States
Catherine
The price is ￥19,347
￥25,242 total
includes taxes & fees
Nov 22 - Nov 23
Meadowood Inn
A large, multi-story house with a snow-covered roof and a prominent tower.

7. 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 ￥19,533
￥23,072 total
includes taxes & fees
Nov 9 - Nov 10
Margaretville Mtn Inn B&B and Village Suites
A house entrance with a red door, a sign reading "Entrance," and a hanging flower basket.

8. Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom.FREE breakfast. Sleeps 2.

Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom.FREE breakfast. Sleeps 2.
Maplecrest
The price is ￥23,455
￥27,556 total
includes taxes & fees
Nov 15 - Nov 16
Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom.FREE breakfast. Sleeps 2.
A wooden deck with a bench, planters with flowers, and a view of a house and trees in the background.

9. Fiddler On The Roof Room<br>Room with mountain views, a King-Size bed, en suite bathroom, and FREE breakfast. It sleeps 2.

Fiddler On The Roof Room<br>Room with mountain views, a King-Size bed, en suite bathroom, and FREE breakfast. It sleeps 2.
Maplecrest
The price is ￥25,040
￥29,439 total
includes taxes & fees
Nov 15 - Nov 16
Fiddler On The Roof Room<br>Room with mountain views, a King-Size bed, en suite bathroom, and FREE breakfast. It sleeps 2.
A wooden deck with a bench, planters with flowers, and a view of a house and trees in the background.

10. Americana Room. Elegant room with a King-Size bed, en suite bathroom, and mountain views. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Americana Room is located on the second floor of Mountain Treasure Bed and Breakfast

Americana Room. Elegant room with a King-Size bed, en suite bathroom, and mountain views. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Americana Room is located on the second floor of Mountain Treasure Bed and Breakfast
Maplecrest
The price is ￥26,292
￥30,964 total
includes taxes & fees
Nov 15 - Nov 16
Americana Room. Elegant room with a King-Size bed, en suite bathroom, and mountain views. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Americana Room is located on the second floor of Mountain Treasure Bed and Breakfast
A large, white, two-story building with a symmetrical facade, central entrance, and columns.

11. 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 ￥37,687
￥41,455 total
includes taxes & fees
Nov 13 - Nov 14
The Queen of the Catskills B&B
A rustic wooden pergola in a garden with a house in the background.

12. 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 ￥31,538
￥35,323 total
includes taxes & fees
Nov 30 - Dec 1
Morning Glory B n B Woodstock NY
Dining

13. GREENE MTN VIEW INN - SLEEPS 28 - FULL INN RENTAL

GREENE MTN VIEW INN - SLEEPS 28 - FULL INN RENTAL
Tannersville
9.0 out of 10, Wonderful, (2 reviews)
"Weekend bachelor party with a group of 35+ year olds. The Inn was just right, everyone had their own room with bathroom and shower, nice feature. This is not the Waldorf or some high end resort, but it didn’t need to be. Five minutes walk to town and the great apple cider donuts at the country K store. We walked across the street to the boat house restaurant and hiking trails for some day time activity. The yard was large so we played corn hole, badminton, and had a camp fire. Overall, we...
United States
Robert C.
The price is ￥190,176
￥248,009 total
includes taxes & fees
Nov 9 - Nov 10
GREENE MTN VIEW INN - SLEEPS 28 - FULL INN RENTAL
A house with a porch and a sign that reads "Kroer Kun bed & breakfast".

14. 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 ￥25,198
￥27,718 total
includes taxes & fees
Nov 15 - Nov 16
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

This is the third time we have stayed here over Thankgiving while visiting relatives in the area. it is such a quiet lovely old house and the owners are very accomodating and exteemly nice. Lots of room, very comfy living room with fireplace and big chairs. The included breakfast is fantastic. The kitchen is always open for tea and homemade cookies. Scent free linens and towels a huge plus.
United States
NH couple
Reviewed November 26, 2016
Albergo Allegria Hotel

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.