Photo by William E Berry Jr.

Find a Bed and Breakfast in Windsor from CA $123

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Windsor B&B

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 "
The price is CA $153
CA $172 total
includes taxes & fees
Aug 25 - Aug 26
Mountain Valley Retreat
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."
The price is CA $210
CA $229 total
includes taxes & fees
Aug 27 - Aug 28
Harvest Barn Inn
The Vesper
Economy Room

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (28)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is CA $234
CA $257 total
includes taxes & fees
Aug 21 - Aug 22
The Vesper
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!"
The price is CA $276
CA $304 total
includes taxes & fees
Aug 28 - Aug 29
Stay At Jimmy's
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (226)
"Great stay! "
The price is CA $292
CA $322 total
includes taxes & fees
Aug 24 - Aug 25
The Jackson
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"
The price is CA $279
CA $304 total
includes taxes & fees
Aug 25 - Aug 26
Stone Hearth Inn and Eatery
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!"
The price is CA $214
CA $259 total
includes taxes & fees
Aug 24 - Aug 25
Snowed 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."
The price is CA $123
CA $215 total
includes taxes & fees
Aug 25 - Aug 26
Room in Historic Inn! 20 Minutes to Okemo!
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. "
The price is CA $178
CA $291 total
includes taxes & fees
Aug 24 - Aug 25
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
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"
The price is CA $313
CA $342 total
includes taxes & fees
Aug 25 - Aug 26
Echo Lake 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"
The price is CA $612
CA $673 total
includes taxes & fees
Sep 15 - Sep 16
Woodbridge Inn
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!"
The price is CA $192
CA $314 total
includes taxes & fees
Aug 24 - Aug 25
King & Queen Suite in Historic Inn Circa 1780
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."
The price is CA $137
CA $230 total
includes taxes & fees
Sep 4 - Sep 5
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

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"This is the 2nd time we stayed here and it's a cute little place. It looks clean and the fresh air is great when you step outside. It does look a little older but nothing that bothers us at all. It had exactly what we needed and would definitely come back again."
David 2-night trip
Posted 2 days ago
Mountain Sports Inn