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

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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, (286 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is 4.520.628 ₫
4.882.278 ₫ total
includes taxes & fees
23 Sept - 24 Sept
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, (137 reviews)
"A fantastic stay!"
United States
David
The price is 3.512.430 ₫
3.793.424 ₫ total
includes taxes & fees
23 Sept - 24 Sept
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, (303 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is 4.318.988 ₫
4.664.507 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Mountain Treasure B&B
A large, multi-story house with a prominent tower, surrounded by a well-maintained lawn and trees.

4. Fairlawn Inn

Fairlawn Inn
3.0 star property
Hunter
8.8 out of 10, Excellent, (441 reviews)
"We had the most lovely stay. It was really cute and the host was so friendly. The breakfast on the wrap around porch was the cherry on top of a great weekend."
United States
Rachel
The price is 6.738.662 ₫
7.277.755 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Fairlawn Inn
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

5. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (318 reviews)
"Been to many hotels up in the catskillls and this place is one of the best! Great amenities, clean spaces, and a really great bar/hotel on site. EV charging stations were a huge plus!"
United States
Karina
The price is 5.268.645 ₫
5.900.882 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Shandaken Inn
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, (300 reviews)
"Wonderful breakfast and friendly atmosphere"
United States
Heidi
The price is 3.176.277 ₫
4.144.147 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Meadowood Inn
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, (87 reviews)
"The host was amazing The breakfast was very good"
United States
john
The price is 4.330.956 ₫
4.764.051 ₫ total
includes taxes & fees
25 Sept - 26 Sept
The Queen of the Catskills B&B
A house with a porch and a sign that reads "Kroer Kun bed & breakfast".

8. River Run Bed and Breakfast

River Run Bed and Breakfast
3.0 star property
Fleischmanns
9.2 out of 10, Wonderful, (210 reviews)
"Excellent stay!!!"
United States
Donna
The price is 4.136.862 ₫
4.550.548 ₫ total
includes taxes & fees
30 Sept - 1 Oct
River Run Bed and Breakfast
A large, multi-story house with a snow-covered roof and a prominent tower.

9. 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, (229 reviews)
"The inn was a dream and the hosts couldn't do enough for each of their guests. I felt welcomed and right at home. Breakfast was delicious and served promptly. I will definitely visit again!"
United States
Lori
The price is 4.032.790 ₫
4.696.249 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Margaretville Mtn Inn B&B and Village Suites
A serene garden with a stone pathway, a small bridge, and a bench.

10. 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, (169 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 5.697.942 ₫
6.381.695 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Morning Glory B n B Woodstock NY
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

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

10/10 Excellent
"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."
Christopher 2-night trip
Posted 7 hours ago
Jimmy OConnors Windham Mountain Inn

Find out more about Windham

Windham B&B information

Number of reviews
1,147
Accommodation
16 B&B
Lowest Price
3.793.424 ₫
Highest Price
7.277.755 ₫

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.
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.

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