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Our top choices for Windsor bed & breakfast

Mountain Valley Retreat

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
Jan 11 - Jan 12, 2026
Total with taxes and fees
Mountain Valley Retreat

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$158 nightly
The price is $172
Jan 4 - Jan 5, 2026
Total with taxes and fees
Harvest Barn Inn

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
$175 nightly
The price is $193
Dec 17 - Dec 18
Total with taxes and fees
The Jackson

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (48)
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
$173 nightly
The price is $191
Jan 15 - Jan 16, 2026
Total with taxes and fees
The Vesper

Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!
Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
$171 nightly
The price is $192
Dec 16 - Dec 17
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
$249 nightly
The price is $274
Dec 16 - Dec 17
Total with taxes and fees
Stay At Jimmy's

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
$200 nightly
The price is $219
Dec 30 - Dec 31
Total with taxes and fees
Stone Hearth Inn and Eatery

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (372)
"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
$241 nightly
The price is $265
Dec 16 - Dec 17
Total with taxes and fees
Snowed Inn

Dexter's 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
$263 nightly
The price is $285
Dec 16 - Dec 17
Total with taxes and fees
Dexter's Inn

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

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Chester Depot
9.0 out of 10, Wonderful, (2)
"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. "
United States
Jacque
$198 nightly
The price is $222
Jan 4 - Jan 5, 2026
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
$268 nightly
The price is $293
Jan 5 - Jan 6, 2026
Total with taxes and fees
Echo Lake Inn

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
$273 nightly
The price is $301
Dec 16 - Dec 17
Total with taxes and fees
Deer Brook Inn

King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780
Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
$221 nightly
The price is $248
Dec 16 - Dec 17
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn
Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
$193 nightly
The price is $216
Dec 16 - Dec 17
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
1,428
Accommodation
26 B&B
Lowest Price
$124
Highest Price
$293

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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