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Compare 33 B&B in Windham with updated reviews, rates, and availability.

Shandaken Inn

4.0 star property
10.0 out of 10, Exceptional, (241)
"Best little inn in the Catskills with plenty to do"
The price is $221
includes taxes & fees
$197 per night
May 1 - May 2
Shandaken Inn

Margaretville Mtn Inn B&B and Village Suites

3.0 star property
8.4 out of 10, Very Good, (196)
"We enjoyed our stay! Very clean and cozy. Delicious breakfast and charming ambiance!"
The price is $132
includes taxes & fees
$120 per night
May 1 - May 2
Margaretville Mtn Inn B&B and Village Suites

Albergo Allegria Hotel & Breakfast Restaurant

3.5 star property
9.6 out of 10, Exceptional, (258)
"Great breakfast, friendly staff."
The price is $160
includes taxes & fees
$148 per night
May 1 - May 2
Albergo Allegria Hotel & Breakfast Restaurant

Meadowood Inn

3.0 star property
9.6 out of 10, Exceptional, (242)
"Tanya was so lovely, attentive and accommodating, we felt right at home even though we only stayed for one night. Would recommend to anyone visiting the area "
The price is $134
includes taxes & fees
$122 per night
May 11 - May 12
Meadowood Inn

River Run Bed and Breakfast

3.0 star property
9.2 out of 10, Wonderful, (188)
"Driving to Bellearye Ski Resort takes only seven minutes, which is convenient for skiers."
The price is $164
includes taxes & fees
$149 per night
May 1 - May 2
River Run Bed and Breakfast

Morning Glory B n B Woodstock NY

3.0 star property
8.4 out of 10, Very Good, (136)
"We absolutely loved our stay - the white room was clean and lovely. We love the location too - great proximity to Station, movie theater and restaurants."
The price is $223
includes taxes & fees
$199 per night
May 5 - May 6
Morning Glory B n B Woodstock NY

Fairlawn Inn

3.0 star property
8.8 out of 10, Excellent, (418)
"Great stay!"
Fairlawn Inn

Arts Inn

3.0 star property
10.0 out of 10, Exceptional, (24)
"Lovely stay. It’s such a cozy spot! "
Arts Inn

Mountain Treasure B&B

3.0 star property
9.4 out of 10, Exceptional, (269)
"This was our second time staying at this property and it was a great stay. Agnes is such a great hostess and the breakfast was fantastic. We will be back again! "
The price is $155
includes taxes & fees
$143 per night
May 1 - May 2
Mountain Treasure B&B

The Queen of the Catskills B&B

3.0 star property
9.2 out of 10, Wonderful, (70)
"Rooms were good size and comfortable. Breakfast was delicious and any time from 6-11 am. Hosts were friendly and accommodating."
The price is $262
includes taxes & fees
$238 per night
May 2 - May 3
The Queen of the Catskills B&B

Coldbrook Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (3)
"This property is gorgeous and the owners did an amazing job at creating a tranquil environment for their guests to enjoy. The check-in process is seamless, the food is delicious, and the rooms are clean and comfortable. We would highly recommend and absolutely come back ourselves. "
Coldbrook Bed and Breakfast

Antique Rose Inn Windham

3.0 star property
9.0 out of 10, Wonderful, (118)
"Nice little B&B. Very friendly host. Would stay again if in the area. "
Antique Rose Inn Windham

Breezy Hill Inn

3.0 star property
10.0 out of 10, Exceptional, (23)
"Nice stay"
Breezy Hill Inn

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 $259
includes taxes & fees
$235 per night
May 1 - May 2
Cozy B&B with WiFi and AC in charming South Kortright

Country Room<br>Inviting, colorful, and cozy room with a Queen Size bed, and en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Country Room is located on the second floor of Mountain Treasure Bed and Break

10.0 out of 10, Exceptional, (1)
"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!"
The price is $172
includes taxes & fees
$159 per night
May 1 - May 2
Country Room<br>Inviting, colorful, and cozy room with a Queen Size bed, and en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Country Room is located on the second floor of Mountain Treasure Bed and Break

Cozy bed & breakfast in delightful South Kortright with WiFi, AC

The price is $231
includes taxes & fees
$210 per night
May 1 - May 2
Cozy bed & breakfast in delightful South Kortright with WiFi, AC

Cozy B&B with WiFi and AC in welcoming South Kortright

10.0 out of 10, Exceptional, (2)
"Came for Hobart Women Writers Festival. Will come again and stay here."
The price is $231
includes taxes & fees
$210 per night
May 1 - May 2
Cozy B&B with WiFi and AC in welcoming South Kortright

Charming 2-bedroom B&B located in South Kortright with AC, WiFi

The price is $402
includes taxes & fees
$365 per night
May 1 - May 2
Charming 2-bedroom B&B located in South Kortright with AC, WiFi

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

8.0 out of 10, Very Good, (1)
The price is $231
includes taxes & fees
$210 per night
May 1 - May 2
Cozy B&B with WiFi and AC in peaceful South Kortright
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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Other property types in Windham

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (98)
"We stayed here for a family wedding and couldn’t have been happier! Rick and Alan were great hosts and super helpful. The property was amazing with so much to offer in and outside of the house. Our kids were obsessed with the pickleball court too ! Highly recommend!"
Tuscan Year Round Beauty - Pickleball Court

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat

Spacious 5-bedroom house in charming Windham centrally located in town.

Spacious 5-bedroom house in charming Windham centrally located in town.
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

What are the most popular Windham B&Bs?
Albergo Allegria Hotel & Breakfast Restaurant is a great choice for travelers seeking a cozy and inviting experience in Windham, boasting an impressive 9.6 rating. This charming Victorian property offers a delightful blend of attentive service and a range of outdoor activities, with easy access to skiing, snowboarding, and hiking right at your doorstep. The ambiance is enhanced by the stunning mountain views, making it a great retreat for couples or anyone looking to unwind after a day of adventure.

For those who appreciate unique decor, the Antique Rose Inn Windham is another excellent option, rated 9.0. This delightful B&B features antique furnishings that create a warm and inviting space. It’s an ideal spot for families or couples wanting to explore the area’s outdoor offerings, including nearby skiing and biking trails. Guests rave about the delicious breakfast, which adds a special touch to the stay.

If you’re looking for a property with a bit of artistic flair, the Georgian Garden Inn, also rated 9.0, offers a stunning view you won’t forget. With an onsite art gallery and a relaxing fireplace, it’s great for business travelers who appreciate a serene environment to unwind after a long day. Outdoor enthusiasts will love the close proximity to hiking and skiing, ensuring that adventure is just a step away.
What is the nightly rate for a Bed and Breakfast in Windham?
Prices for B&Bs in Windham often vary, but you can find a great deal from $132 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
Are there any family-friendly Bed & Breakfasts in Windham?
Albergo Allegria Hotel & Breakfast Restaurant is a fantastic choice for families visiting Windham. This charming property offers thoughtfully designed accommodations, featuring sofa beds and child-friendly window designs, ensuring that your little ones are safe and comfortable. Families will appreciate the complimentary cribs and the daily housekeeping service, which allows you more time to enjoy your vacation. The inviting garden provides a lovely space for kids to play while adults can relax, and the breakfast menu includes special options tailored for children, making the morning routine a delightful experience for everyone.

Another wonderful family-friendly option is the Antique Rose Inn Windham. This delightful B&B also offers complimentary cribs and a serene garden, great for unwinding after a day of adventures. With daily housekeeping, the inn ensures that your family can enjoy a clutter-free space to recharge for the next day’s explorations. The warm and friendly space of the Antique Rose Inn makes it an ideal retreat for families looking to create lasting memories in the beautiful surroundings of Windham.
Do any Windham Bed & Breakfasts allow dogs?
Albergo Allegria Hotel & Breakfast Restaurant is a charming option in Windham that welcomes dogs, ensuring a delightful stay for pet owners. Nestled in a historical district, this Victorian property combines classic elegance with modern conveniences. Guests can enjoy breathtaking mountain views from the furnished patio, superb for relaxing after a day of adventure.
When is the best time to book a B&B in Windham?
The most popular time to book a B&B in Windham is during the winter months, particularly from December to February. This peak season draws visitors seeking thrilling outdoor activities, such as skiing and snowboarding, on the beautiful slopes of Windham Mountain. With ample snowfall and well-groomed trails, the area becomes a winter wonderland, superb for both seasoned enthusiasts and beginners alike.

January, in particular, offers a fantastic experience, with average temperatures ranging from the mid-20s to low 30s Fahrenheit. Visitors can revel in the crisp mountain air while exploring the charming local shops or warming up in cozy cafes. The festive atmosphere during this month enhances the overall experience, making it an ideal time for family trips or romantic getaways.

For those looking to enjoy Windham without the hustle and bustle, consider visiting in October. This month showcases the breathtaking fall foliage, creating picturesque landscapes superb for hiking and photography. With fewer crowds, you can fully immerse yourself in the tranquility of nature while enjoying the vibrant colors of autumn.
What is the difference between a Windham Bed & Breakfast and a hotel?
Every Windham B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windham B&Bs.