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Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14
In one month
Dec 26 - Dec 28
In two months
Jan 23 - Jan 25

B&B in Windsor

Exterior
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
Nov 30 - Dec 1
Total with taxes and fees
Mountain Valley Retreat
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (251)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
$175 nightly
The price is $193
Nov 30 - Dec 1
Total with taxes and fees
The Jackson
Front of property
Snowed Inn

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
$195 nightly
The price is $214
Dec 3 - Dec 4
Total with taxes and fees
Snowed Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
$202 nightly
The price is $221
Dec 22 - Dec 23
Total with taxes and fees
Stone Hearth Inn and Eatery
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (17)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
$149 nightly
The price is $167
Nov 30 - Dec 1
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi
The Vesper

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (46)
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
$163 nightly
The price is $180
Dec 1 - Dec 2
Total with taxes and fees
The Vesper
Dining
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
$144 nightly
The price is $161
Nov 30 - Dec 1
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Game room
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
$248 nightly
The price is $269
Dec 1 - Dec 2
Total with taxes and fees
Dexter's Inn
Front of property
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
Nov 30 - Dec 1
Total with taxes and fees
Stay At Jimmy's
Outdoor pool
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
$274 nightly
The price is $299
Dec 16 - Dec 17
Total with taxes and fees
Echo Lake Inn
Front of property - evening/night
Woodbridge Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67)
"Staff was very friendly and welcoming "
United States
Michael
$445 nightly
The price is $490
Dec 11 - Dec 12
Total with taxes and fees
Woodbridge Inn
1 bedroom, desk, iron/ironing board, free WiFi
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.
$194 nightly
The price is $217
Nov 30 - Dec 1
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Interior
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.
$363 nightly
The price is $407
Nov 26 - Nov 27
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
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
"Clean good service and location "
Thomas 1-night trip
Posted 2 days ago
The Shire Woodstock

Find out more about Windsor

Windsor B&B information

Number of reviews
1,240
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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