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B&B in Windsor

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
$110 nightly
The price is $124
Nov 17 - Nov 18
Total with taxes and fees
Mountain Valley Retreat

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (247)
"The room, the staff, the amenities were what we were hoping for. The Jackson is a great place to stay! "
United States
Frederick
$175 nightly
The price is $193
Nov 18 - Nov 19
Total with taxes and fees
The Jackson

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
$135 nightly
The price is $151
Nov 17 - Nov 18
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Room was super quiet and clean. "
United States
Ernest
$207 nightly
The price is $226
Dec 1 - Dec 2
Total with taxes and fees
Stone Hearth Inn and Eatery

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
$199 nightly
The price is $219
Nov 17 - Nov 18
Total with taxes and fees
Stay At Jimmy's

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

Chester Depot
9.0 out of 10, Wonderful, (2)
"Yes, wonderful location and stay"
United States
Sharon
$144 nightly
The price is $161
Nov 17 - Nov 18
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (44)
"The Vesper was a great find in Woodstock VT. Close to downtown to walk to everything. Rooms are spotless and charming. We would definitely stay at the Vesper BnB again."
United States
Kevin
$163 nightly
The price is $180
Nov 18 - Nov 19
Total with taxes and fees
The Vesper

Snowed Inn

3.5 star property
Killington
9.8 out of 10, Exceptional, (370)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
United States
Bradford
$227 nightly
The price is $249
Dec 3 - Dec 4
Total with taxes and fees
Snowed Inn

Dexter's Inn

3.0 star property
Sunapee
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. "
United States
Lisa
$235 nightly
The price is $256
Dec 1 - Dec 2
Total with taxes and fees
Dexter's Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (66)
"Amazing stay at a beautiful location. Would definitely stay again. "
United States
Aaron
$445 nightly
The price is $490
Dec 11 - Dec 12
Total with taxes and fees
Woodbridge Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"The staff was super friendly, and welcoming "
United States
Janet
$277 nightly
The price is $302
Nov 24 - Nov 25
Total with taxes and fees
Echo Lake Inn

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
$202 nightly
The price is $226
Nov 17 - Nov 18
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
$159 nightly
The price is $178
Nov 17 - Nov 18
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
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

Find out more about Windsor

Windsor B&B information

Number of reviews
1,235
Accommodation
24 B&B
Lowest Price
$124
Highest Price
$490

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.

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