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Book Windsor Bed & Breakfast

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Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

B&B in Windsor

The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (225)
"Great stay! "
$248 nightly
The price is $273
Aug 18 - Aug 19
Total includes taxes and fees
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (358)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
$170 nightly
The price is $187
Aug 17 - Aug 18
Total includes taxes and fees
Snowed Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (182)
"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "
$110 nightly
The price is $124
Aug 17 - Aug 18
Total includes taxes and fees
Mountain Valley Retreat
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (27)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
$165 nightly
The price is $182
Aug 21 - Aug 22
Total includes taxes and fees
The Vesper
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
Stone Hearth Inn and Eatery
Front of property

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 18 - Aug 19
Total includes taxes and fees
Stone Hearth Inn and Eatery
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (39)
"Superb stay in all ways!"
$199 nightly
The price is $219
Aug 17 - Aug 18
Total includes taxes and fees
Stay At Jimmy's
Harvest Barn Inn
Porch

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."
$190 nightly
The price is $207
Sep 4 - Sep 5
Total includes taxes and fees
Harvest Barn Inn
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
$441 nightly
The price is $485
Sep 15 - Sep 16
Total includes taxes and fees
Woodbridge Inn
Golden Stage Inn B&B
Seasonal outdoor pool

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
Echo Lake Inn
Outdoor pool

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"
$221 nightly
The price is $241
Aug 18 - Aug 19
Total includes taxes and fees
Echo Lake Inn
The Woodstocker B&B
Exterior

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
1 bedroom, desk, iron/ironing board, free WiFi

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!
Dining

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 17 - Aug 18
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
Interior

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 18 - Aug 19
Total includes taxes and fees
King & Queen Suite in Historic Inn Circa 1780
Dexter's Inn
Game room

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!
Terrace/patio

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
Terrace/patio

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
Inn at Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."
Cheryl 2-night trip
Posted 2 days ago
The Shire Woodstock

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.