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Book Windsor Bed & Breakfast

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Oct 31 - Nov 2
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Nov 21 - Nov 23
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B&B in Windsor

Porch
Harvest Barn Inn
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (241)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$136 nightly
The price is $149
Nov 20 - Nov 21
Total with taxes and fees
Harvest Barn Inn
Exterior
Mountain Valley Retreat
Mountain Valley Retreat
2.5 star property
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
$110 nightly
The price is $124
Oct 27 - Oct 28
Total with taxes and fees
Mountain Valley Retreat
Front of property
The Jackson
The Jackson
4.0 star property
9.8 out of 10, Exceptional, (238)
"Excellent Vintage style B&B. "
United States
Yinghua
$175 nightly
The price is $193
Nov 4 - Nov 5
Total with taxes and fees
The Jackson
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi
The Vesper
The Vesper
3.0 star property
9.0 out of 10, Wonderful, (40)
"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
Oct 28 - Oct 29
Total with taxes and fees
The Vesper
Iron/ironing board, travel crib, WiFi, bed sheets
Sleep Woodstock - Dog Friendly King Suite
Sleep Woodstock - Dog Friendly King Suite
10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
United States
Julie R.
$179 nightly
The price is $197
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (103)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
$223 nightly
The price is $244
Nov 24 - Nov 25
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!
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 2 - Nov 3
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Iron/ironing board, travel crib, WiFi, bed sheets
Sleep Woodstock - 2 Double Beds - Dog Friendly
Sleep Woodstock - 2 Double Beds - Dog Friendly
10.0 out of 10, Exceptional, (2)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
United States
stacey a.
$170 nightly
The price is $188
Oct 29 - Oct 30
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Front of property
Snowed Inn
Snowed Inn
3.5 star property
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
$231 nightly
The price is $254
Oct 28 - Oct 29
Total with taxes and fees
Snowed Inn
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!
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 2 - Nov 3
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Front of property
Stay At Jimmy's
Stay At Jimmy's
3.0 star property
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
$199 nightly
The price is $219
Nov 2 - Nov 3
Total with taxes and fees
Stay At Jimmy's
Iron/ironing board, travel crib, WiFi, bed sheets
Sleep Woodstock Mobility Impaired Accessible Suite
Sleep Woodstock Mobility Impaired Accessible Suite
$166 nightly
The price is $182
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
Outdoor pool
Echo Lake Inn
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (98)
"Charming place, the food was great, rooms clean, and service was excellent"
United States
Erik
$277 nightly
The price is $302
Nov 24 - Nov 25
Total with taxes and fees
Echo Lake Inn
Interior
King & Queen Suite in Historic Inn Circa 1780
King & Queen Suite in Historic Inn Circa 1780
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.
$203 nightly
The price is $227
Nov 4 - Nov 5
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
$159 nightly
The price is $178
Nov 2 - Nov 3
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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"The hotel is located up a hill in a nice town, and is very peaceful and quiet. The room was clean. I have no complaints. I would definitely stay here again."
Shelly 1-night trip
Posted 10 hours ago
North Star Lodge and Resort

Find out more about Windsor

Windsor B&B information

Number of reviews
1,335
Accommodation
24 B&B
Lowest Price
$124
Highest Price
$302

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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