Bed and Breakfast in Windham

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured B&B in Windham

Shandaken Inn
Seasonal outdoor pool
Shandaken Inn
4.0 star property
10.0 out of 10, Exceptional, (200)
"Very beautiful & quiet spot for a relaxing weekend."
The price is NZ$385
includes taxes & fees
25 Sept - 26 Sept
Shandaken Inn
Margaretville Mtn Inn B&B and Village Suites
Front of property - evening/night
Margaretville Mtn Inn B&B and Village Suites
3.0 star property
8.2 out of 10, Very good, (183)
"Could have used some heat. Breakfast delicious Needs an upgrade"
The price is NZ$248
includes taxes & fees
30 Sept - 1 Oct
Margaretville Mtn Inn B&B and Village Suites
Meadowood Inn
Front of property
Meadowood Inn
3.0 star property
9.6 out of 10, Exceptional, (203)
"Loved it"
The price is NZ$216
includes taxes & fees
22 Sept - 23 Sept
Meadowood Inn
Fairlawn Inn
Exterior
Fairlawn Inn
3.0 star property
8.8 out of 10, Excellent, (408)
"Very friendly and helpful concierge. "
The price is NZ$346
includes taxes & fees
21 Sept - 22 Sept
Fairlawn Inn
The Queen of the Catskills B&B
Front of property
The Queen of the Catskills B&B
3.0 star property
9.2 out of 10, Wonderful, (66)
"The property and hostess were wonderful. I felt like we were treated like family and were made completely comfortable. Room 1, with its own bathroom, was comfortable and functional, although we had trouble with the television, which could use some instructions. As we were the only guests at the time, the ingredients were purchased and our breakfast made to order. Delicious with caring touches and presentation. The house is showing its character in age a little bit, but that simply adds to...
The price is NZ$375
includes taxes & fees
1 Oct - 2 Oct
The Queen of the Catskills B&B
Albergo Allegria Hotel & Breakfast Restaurant
Front of property
Albergo Allegria Hotel & Breakfast Restaurant
3.5 star property
9.6 out of 10, Exceptional, (243)
"Albergo Alegria Hotel is lovely (although the name is hard to remember). The room was very comfortable. Breakfast on the porch is fantastic. "
The price is NZ$277
includes taxes & fees
21 Oct - 22 Oct
Albergo Allegria Hotel & Breakfast Restaurant
Mountain Treasure B&B
Exterior
Mountain Treasure B&B
3.0 star property
9.4 out of 10, Exceptional, (254)
"Anges was an amazing host! Mountain Treasure Bed and Breakfast" was fantastic, and the creek and its surroundings gave it the perfect touch. Anges is well versed with many activities (hiking, canoeing, swimming), attractions (historic sites), restaurants, etc. nearby. If you want a nice and quiet experience or outdoor excitement, Mountain Treasure B&B will not disappoint. Thank you, Anges! P.S. The chickens were friendly too.. lol!"
The price is NZ$253
includes taxes & fees
22 Sept - 23 Sept
Mountain Treasure B&B
River Run Bed and Breakfast
Front of property
River Run Bed and Breakfast
3.0 star property
9.2 out of 10, Wonderful, (173)
"Thank you Adam and Ben for a great stay in the beautiful Catskills. We really enjoyed your cozy inn. Breakfasts were fresh and delicious. Our room was clean and comfortable. We liked the little village and your eclectic collection. We would highly recommend your B&B to anyone wishing to explore the area."
The price is NZ$264
includes taxes & fees
30 Sept - 1 Oct
River Run Bed and Breakfast
Antique Rose Inn Windham
Front of property
Antique Rose Inn Windham
3.0 star property
9.2 out of 10, Wonderful, (113)
" Very comfortable bed, terrific breakfast on the wrap around porch. Wonderful area, Love Windham, charming town. Will b back."
The price is NZ$234
includes taxes & fees
23 Sept - 24 Sept
Antique Rose Inn Windham
Morning Glory B n B Woodstock NY
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property
Morning Glory B n B Woodstock NY
3.0 star property
8.4 out of 10, Very good, (125)
"The proprietor and her mom are wonderful hosts. The property is pretty. The rooms are very clean and there was a full hot breakfast and was made to order. This was the second time U stayed here. I would definitely return. "
The price is NZ$358
includes taxes & fees
23 Sept - 24 Sept
Morning Glory B n B Woodstock NY
The Bavarian Manor Hotel
View from property
The Bavarian Manor Hotel
2.5 star property
8.0 out of 10, Very good, (410)
"Second time staying here and just love the charm of the inn. Will be back!"
The Bavarian Manor Hotel
Arts Inn
Hiking
Arts Inn
3.0 star property
10.0 out of 10, Exceptional, (20)
"Arts Inn is clearly a "10". Randy and Heidi are wonderful hosts. They know the area very well and gave us great recommendations for dining, hiking and and other activities in the area. You will feeling completely at home in this beautiful Inn. Wonderful breakfast, immaculate house and grounds and quiet surroundings. Will definitely stay here again. "
Arts Inn
Breezy Hill Inn
Front of property - evening/night
Breezy Hill Inn
3.0 star property
10.0 out of 10, Exceptional, (19)
"A very charming Inn in a beautiful location. The only issue I had was the temperature of the room. It was very warm and a little uncomfortable . No obvious way to cool the interior in room. Other than that, very nice stay. "
The price is NZ$363
includes taxes & fees
21 Sept - 22 Sept
Breezy Hill Inn
Georgian Garden Inn
Front of property
Georgian Garden Inn
3.0 star property
9.0 out of 10, Wonderful, (28)
"We had a comfortable and lovely stay. The hostesses Viktoria and Irina were very hospitable, friendly and helpful, if you have any questions feel free to ask them. The property has a great location, it is close to the center of Windhem. Our room was clean, comfortable, with beautiful view and excellent internet service. Glad we chose Georgian Garden, highly recommended."
Georgian Garden Inn
Cozy B&B with WiFi and AC in peaceful South Kortright
Exterior
Cozy B&B with WiFi and AC in peaceful South Kortright
The price is NZ$360
includes taxes & fees
19 Oct - 20 Oct
Cozy B&B with WiFi and AC in peaceful South Kortright
Charming 2-bedroom B&B located in South Kortright with AC, WiFi
Exterior
Charming 2-bedroom B&B located in South Kortright with AC, WiFi
The price is NZ$634
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom B&B located in South Kortright with AC, WiFi
Cozy bed & breakfast in delightful South Kortright with WiFi, AC
Exterior
Cozy bed & breakfast in delightful South Kortright with WiFi, AC
The price is NZ$360
includes taxes & fees
19 Oct - 20 Oct
Cozy bed & breakfast in delightful South Kortright with WiFi, AC
Cozy B&B with WiFi and AC in welcoming South Kortright
Exterior
Cozy B&B with WiFi and AC in welcoming South Kortright
10.0 out of 10, Exceptional, (1)
"Came for Hobart Women Writers Festival. Will come again and stay here."
The price is NZ$352
includes taxes & fees
20 Oct - 21 Oct
Cozy B&B with WiFi and AC in welcoming South Kortright
Cozy B&B with WiFi and AC in charming South Kortright
Exterior
Cozy B&B with WiFi and AC in charming South Kortright
10.0 out of 10, Exceptional, (1)
"Lovely place., lovely owners. Very accomadating. Clean, well appointed. Excellent restaurant as well. We would be happy to be there again."
The price is NZ$398
includes taxes & fees
19 Oct - 20 Oct
Cozy B&B with WiFi and AC in charming South Kortright
Cozy B&B with WiFi and AC in charming South Kortright
Exterior
Cozy B&B with WiFi and AC in charming South Kortright
The price is NZ$339
includes taxes & fees
19 Oct - 20 Oct
Cozy B&B with WiFi and AC in charming South Kortright
Don't see what you're looking for?
See all available properties in Windham
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windham

Tuscan Year Round Beauty - Pickleball Court
Outdoor dining
Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (93)
"Rick was an amazing host and the property exceeded expectations and the views are amazing. Well worth it. "
Tuscan Year Round Beauty - Pickleball Court
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (139)
"The property is so so good for large groups. Compared to other large bnbs, this house feels so much more set up for big groups, with a full kitchen and plenty of space. Greg is an awesome host! I highly recommend this space 💕"
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
Fridge, microwave, oven, stovetop
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
9.8 out of 10, Exceptional, (6)
"We could not have had a more comfotable stay! Bridget was quick to respond and ver helpful. The place easily fit our party of 13. We all had a restful weekend. Lots to do nearby but also no reason to want to leave this beatiful home. Highly reccomend!!!"
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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.

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 & Breakfast Restaurant: 21 rooms. Enjoy the unique decor and library. Antique Rose Inn Windham: 3 rooms. Enjoy the free full breakfast and unique decor. Georgian Garden Inn: 5 rooms. Enjoy the sauna and fireplace in reception.
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 April, 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 Ashland 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.