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
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

Our top choices for Windham bed & breakfast

Front of property

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (133 reviews)
"A fantastic stay!"
United States
David
The price is AED 496
AED 536 total
includes taxes & fees
22 Jun - 23 Jun
Antique Rose Inn Windham
Front of property

Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (281 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is AED 597
AED 645 total
includes taxes & fees
23 Jun - 24 Jun
Albergo Allegria Hotel
Front of property

Meadowood Inn

Meadowood Inn
3.0 star property
Arkville
9.6 out of 10, Exceptional, (285 reviews)
"Tanya was very helpful and breakfast was excellent! "
United States
Beth
The price is AED 448
AED 493 total
includes taxes & fees
25 Jun - 26 Jun
Meadowood Inn
Free daily local cuisine breakfast

Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (286 reviews)
"The staff were wonderful, the Inn is cozy and well maintained. It’s very pet friendly and the meals were excellent. One thing we missed is having coffee/tea available if you’re up before breakfast."
United States
Lisa
The price is AED 757
AED 848 total
includes taxes & fees
7 Jul - 8 Jul
Shandaken Inn
Property amenity

Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (295 reviews)
"The room was clean and comfortable, the breakfast was great. We had a good stay. "
United States
cynthia
The price is AED 546
AED 590 total
includes taxes & fees
22 Jun - 23 Jun
Mountain Treasure B&B
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property

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, (160 reviews)
"Wonderful facility Very welcoming Delicious breakfast Within walking distance of shops and restaurants"
United States
John
The price is AED 731
AED 819 total
includes taxes & fees
22 Jun - 23 Jun
Morning Glory B n B Woodstock NY
Front of property

The Queen of the Catskills B&B

The Queen of the Catskills B&B
3.0 star property
Stamford
9.2 out of 10, Wonderful, (79 reviews)
"Amazing breakfast, great bedroom and amenities. The owners were lovely, extremely attentive and went out of their way to make the stay incredibly memorable and stress-free."
United States
Joseph
The price is AED 786
AED 865 total
includes taxes & fees
26 Jun - 27 Jun
The Queen of the Catskills B&B
Outdoor dining

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, (1 review)
"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 AED 511
AED 631 total
includes taxes & fees
22 Jun - 23 Jun
Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.
Exterior detail

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 AED 544
AED 674 total
includes taxes & fees
28 Jun - 29 Jun
Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom.FREE breakfast. Sleeps 2.
Terrace/patio

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 AED 580
AED 718 total
includes taxes & fees
23 Jun - 24 Jun
Fiddler On The Roof Room<br>Room with mountain views, a King-Size bed, en suite bathroom, and FREE breakfast. It sleeps 2.
Terrace/patio

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 AED 609
AED 753 total
includes taxes & fees
28 Jun - 29 Jun
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
Front of property

River Run Bed and Breakfast

River Run Bed and Breakfast
3.0 star property
Fleischmanns
9.2 out of 10, Wonderful, (203 reviews)
"Such a quaint bed and breakfast. Of course it’s old house, but very clean. Breakfast was delicious and staff is very friendly and accommodating. "
United States
Sandra
The price is AED 584
AED 642 total
includes taxes & fees
28 Jun - 29 Jun
River Run Bed and Breakfast
Exterior

Fairlawn Inn

Fairlawn Inn
3.0 star property
Hunter
8.8 out of 10, Excellent, (437 reviews)
"Lovely stay"
United States
Deborah
The price is AED 1,025
AED 1,107 total
includes taxes & fees
11 Jul - 12 Jul
Fairlawn 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.
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"This lodge is very cozy very clean and great views. Staff was very helpful/ friendly . Such a cute mini getaway spot. Will for sure be coming back"
Ramona 1-night trip
Posted 20 hours ago
Hunter Lodge, a Bluebird by Lark

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.