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Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Windsor

The Jackson
Step out onto the covered porch, surrounded by lush greenery and a brick pathway leading to the house.

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (223)
"A quaint boutique historic hotel with a cool little bar and fine dining. The view from our room overlooking the garden and lush lawn added to the tranquil atmosphere that we were hoping for. The owners were pleasant and friendly. "
$248 nightly
The price is $273
Aug 6 - Aug 7
Total includes taxes and fees
The Jackson
Snowed Inn
Step into the warm and inviting entrance of this charming lodge, featuring a stone facade and wooden beams.

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (356)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
$170 nightly
The price is $187
Aug 7 - Aug 8
Total includes taxes and fees
Snowed Inn
Stay At Jimmy's
Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (38)
"Superb stay in all ways!"
$299 nightly
The price is $329
Aug 11 - Aug 12
Total includes taxes and fees
Stay At Jimmy's
The Vesper
Relax in this serene bedroom with a large bed, two windows, and a cozy reading nook.

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (27)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
$182 nightly
The price is $201
Aug 18 - Aug 19
Total includes taxes and fees
The Vesper
Mountain Valley Retreat
Stunning two-story house with a gabled roof and wrap-around porch, set amidst a beautifully manicured lawn and lush trees.

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (181)
"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "
$110 nightly
The price is $124
Aug 5 - Aug 6
Total includes taxes and fees
Mountain Valley Retreat
Harvest Barn Inn
Enjoy a serene lake view from the balcony, where two Adirondack chairs await.

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
$141 nightly
The price is $154
Aug 19 - Aug 20
Total includes taxes and fees
Harvest Barn Inn
Stone Hearth Inn and Eatery
Traditional home with a charming porch surrounded by lush gardens and a brick chimney.

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (92)
"Sweet place to stay"
$224 nightly
The price is $244
Aug 6 - Aug 7
Total includes taxes and fees
Stone Hearth Inn and Eatery
The Buckmaster Inn
Charming two-story house with a welcoming front porch and a red door.

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
Woodbridge Inn
Cozy home with a charming porch, blue door, and string lights.

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
Woodbridge Inn
Echo Lake Inn
Relax by the pool surrounded by a charming white picket fence and comfortable lounge chairs.

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
$210 nightly
The price is $229
Aug 11 - Aug 12
Total includes taxes and fees
Echo Lake Inn
Golden Stage Inn B&B
Relax by the pool surrounded by lush greenery and trees, with lounge chairs and umbrellas providing shade.

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Very beautiful place and excellent service "
Golden Stage Inn B&B
The Woodstocker B&B
Charming single-story home with a welcoming porch and lush green surroundings.

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (51)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
The Woodstocker B&B
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Relax in a cozy seating area with a sofa and coffee table, and enjoy a compact kitchenette with microwave and refrigerator.

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
$149 nightly
The price is $167
Sep 1 - Sep 2
Total includes taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Enjoy a classic dining experience with a traditional table and chairs, surrounded by decorative plates and ceramics.

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very Good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
$188 nightly
The price is $211
Aug 5 - Aug 6
Total includes taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Relax in style with a comfortable seating area, fireplace, and dining space, perfect for leisure activities and enjoying a view of the outdoors.

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (15)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
$203 nightly
The price is $227
Aug 6 - Aug 7
Total includes taxes and fees
King & Queen Suite in Historic Inn Circa 1780
Dexter's Inn
Enjoy a game of ping pong in this cozy room with a scenic view of the snowy landscape.

Dexter's Inn

3.0 star property
8.8 out of 10, Excellent, (70)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
Dexter's Inn
Room in Historic Inn! 20 Minutes to Okemo!
Relax on the porch with wicker chairs and a small table, surrounded by windows with shutters.

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (16)
"My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again."
$139 nightly
The price is $156
Aug 24 - Aug 25
Total includes taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Windsor Mansion Inn
Front of property - evening/night

Windsor Mansion Inn

3.5 star property
9.2 out of 10, Wonderful, (289)
"We had a lovely time at the Windsor Mansion Inn over New Years! Andy was incredible accommodating and friendly to make our group feel right at home. The beds were very comfortable the the rooms were spacious. The mansion is gorgeous. Yummy breakfast too. We hope to stay again!"
Windsor Mansion Inn
Deer Brook Inn
Relax in style with a patio featuring a table for two, wicker chairs, and a beautiful garden view.

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!"
Deer Brook Inn
Rockledge Farm country living
Stroll through a serene garden featuring lush greenery, a well-maintained lawn, and mature trees surrounding a charming porch.

Rockledge Farm country living

9.8 out of 10, Exceptional, (29)
"Kathleen was a joy; friendly, accommodating and a wonderful cook."
Rockledge Farm country living
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 Windsor Hotel Reviews

Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

10/10 Excellent
"The staff was very friendly and helpful. The room was nice and clean. Comfy beds. Breakfast was good and fast."
Melanie 1-night trip
Posted 2 days ago
Courtyard by Marriott Hanover Lebanon

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Windsor?
Prices for B&Bs in Windsor often vary, but you can find a great deal from $124 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor 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.
When is the best time to book a Bed & Breakfast in Windsor?
The best time to book a B&B in Windsor is during the late spring and summer months, particularly from May through September. This peak season invites travelers to immerse themselves in the vibrant local culture, with numerous outdoor festivals and events that showcase the area's charm and hospitality. The pleasant weather, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit, makes it an ideal backdrop for leisurely strolls along the waterfront, wine tasting tours, and exploring the nearby parks.

June is particularly popular, as it heralds the start of summer festivities, including music events and farmers' markets brimming with fresh local produce. The lively atmosphere of the town, combined with the colorful gardens in full bloom, offers a delightful experience for those seeking to connect with the community.

For those looking for a more budget-friendly option, consider visiting in late fall, around November. This time offers a quieter ambiance, great for enjoying the beautiful autumn foliage and indulging in local culinary delights without the hustle and bustle of peak tourist season.
What is the difference between a Windsor B&B and a hotel?
Every Windsor 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 Windsor B&Bs.