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B&B in Windsor

"Excellent Vintage style B&B. "

$430 nightly

Sep 28 - Sep 29

Total with taxes and fees

Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"

$281 nightly

Oct 22 - Oct 23

Total with taxes and fees

"Beautiful place to stay! 10/10 would recommend. You're going to love it!"

$163 nightly

Sep 23 - Sep 24

Total with taxes and fees

"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "

$155 nightly

Sep 25 - Sep 26

Total with taxes and fees

"Sweet place to stay"

$242 nightly

Sep 23 - Sep 24

Total with taxes and fees

"Elizabeth and Richard are amazing people and welcomed us into their home. The property is beautifully maintained and Elizabeth's cooking is top notch. "

"Absolutely lovely stay!"

$120 nightly

Oct 21 - Oct 22

Total with taxes and fees

"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"

$349 nightly

Sep 24 - Sep 25

Total with taxes and fees

"Staff was very friendly and welcoming "

$441 nightly

Sep 23 - Sep 24

Total with taxes and fees

"Very beautiful place and excellent service "

"Charming place, the food was great, rooms clean, and service was excellent"

1 bedroom, desk, iron/ironing board, free WiFi

"Charming place, hope to go back soon."

$174 nightly

Sep 23 - Sep 24

Total with taxes and fees

"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "

"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"

$231 nightly

Sep 23 - Sep 24

Total with taxes and fees

"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. "

$210 nightly

Sep 23 - Sep 24

Total with taxes and fees

"The room was fine. Bright night lights outside require eye masks for dark sleeping. The shower unit was a bit odd… not a conventional shower stall. The bottom fitted sheet did not stay on the mattress."

$205 nightly

Sep 25 - Sep 26

Total with taxes and fees

"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. "

"One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!"

"We had a lovely time at the Windsor Mansion Inn over New Years! Andy was incredible accommodating and friendly to make our group feel right at home. The beds were very comfortable the the rooms were spacious. The mansion is gorgeous. Yummy breakfast too. We hope to stay again!"

"Kathleen was a joy; friendly, accommodating and a wonderful cook."

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Top Windsor Hotel Reviews

Align Inn Vermont

10/10 Excellent

"Best hotel in the area, feels like home, the staff are so warm and welcoming, especially Chelsea. She gave us so many local recommendations, the Mexican restaurant next door is excellent. The rooms and cozy and clean. "

Mountain Sports Inn

10/10 Excellent

"An absolutely amazing place to stay. The rooms I loved. I get so tired of the regular cookie cutter fancy hotel rooms. This is a ski lodge and it's designed and decorated as such. The staff is super friendly. There is adequate parking outside. It's in a beautiful area with restaurants and bars within driving distance The breakfast options were very plentiful Continental breakfast and it included fruit three different kinds of cereal a few different kinds of bagels muffins donuts there was some orange juice hot tea and coffee more than enough.. I will definitely be back it was a great place to stay and the beds were so comfortable It was one of the most comfortable beds I've ever slept in"

Find out more about Windsor

Windsor B&B information

Number of reviews	1,487
Accommodation	24 B&B
Lowest Price	$136
Highest Price	$485

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 $136 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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B&B in Windsor

The Jackson

The Jackson

The Vesper

The Vesper

Snowed Inn

Snowed Inn

Harvest Barn Inn

Harvest Barn Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

The Buckmaster Inn

The Buckmaster Inn

Mountain Valley Retreat

Mountain Valley Retreat

Stay At Jimmy's

Stay At Jimmy's

Woodbridge Inn

Woodbridge Inn

Golden Stage Inn B&B

Golden Stage Inn B&B

Echo Lake Inn

Echo Lake Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

The Woodstocker B&B

The Woodstocker B&B

King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

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!

Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Dexter's Inn

Dexter's Inn

Deer Brook Inn

Deer Brook Inn

Windsor Mansion Inn

Windsor Mansion Inn

Rockledge Farm country living

Rockledge Farm country living

Top Windsor Hotel Reviews

Align Inn Vermont

Find out more about Windsor

Find out more about Windsor

Windsor B&B information

Frequently asked questions

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