Photo by William E Berry Jr.

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Compare 19 Guest Houses in Windsor with updated reviews, rates, and availability.

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (130)
"Great place. We will be back!"
The Trailside Inn

Brook Road Inn

3.0 star property
8.8 out of 10, Excellent, (214)
"This is my 2nd stay at the inn. Between this stay and the last one, the incidentals deposit handling changed and I never received the check in email. Had I not known I should have received the email to get the code (after paying the deposit) to get into the building and called before I arrived, I would have been stuck. Fortunately I knew it was missing. The service rep handled the situation perfectly. Aside from that bump, we still love the facility’s charm. Just remember it’s an old home not...
The price is AED 257
AED 407 total
includes taxes & fees
1 May - 2 May
Brook Road Inn

Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants

9.8 out of 10, Exceptional, (42)
"Perfect location and very clean!"
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants

Inn at Clearwater Pond (Quechee)

3.5 star property
9.4 out of 10, Exceptional, (45)
"AMAZING STAY AMAZING PLACE"
Inn at Clearwater Pond (Quechee)

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

9.6 out of 10, Exceptional, (36)
"We stayed for 20 days in January to enjoy skiing at Okemo, which was a short trip from the Carriage House. It was better than described on the listing with more amenities than expected. The kitchen was stocked with everything needed for cooking and baking-except for the groceries. The modern appliances and crockpot allowed me to cook with ease. Having a washer/dryer on site, as well as detergent, was very convenient. Hosts Jennifer and Michael provide a detailed description of how everything...
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!

10.0 out of 10, Exceptional, (2)
"Our group had a wonderful stay. The ski out location is great and worked well even for our beginning skiers. The amenities were as described and the views are amazing. The property owner was extremely responsive when a minor issue arose. We highly recommend!"
The price is AED 1,418
AED 3,194 total
includes taxes & fees
1 May - 2 May
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!

Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

9.4 out of 10, Exceptional, (33)
"Overall a great place in a beautiful area next to a skii hill. There were issues with bugs throughout the place when we first arrived. Its important to note there is no mobile service within a mile of this place so make sure to have your wifi and checkin details available. Some parts of the room were dusty and had cobwebs but the owner did have plenty of towels and supplies to make our stay great."
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

Mountain View / Brook Road Inn

9.8 out of 10, Exceptional, (8)
"Everything was perfect! Cozy place, comfy bed, hot shower, coffee in the am and location was perfect for skiing!"
The price is AED 298
AED 530 total
includes taxes & fees
1 May - 2 May
Mountain View / Brook Road Inn

110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

8.0 out of 10, Very Good, (5)
"Beds not terrible. Sofa bed very terrible. Great pool. Reasanable price vs quality. Renovated in pass years. Clean place"
The price is AED 382
AED 578 total
includes taxes & fees
18 May - 19 May
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

Red,White & Blue/Brook Road Inn

9.6 out of 10, Exceptional, (8)
"Nice but be carefull. I thought I booked two beds."
The price is AED 275
AED 506 total
includes taxes & fees
1 May - 2 May
Red,White & Blue/Brook Road Inn

Blue Goose / Brook Road Inn

9.6 out of 10, Exceptional, (7)
"Check in was easy, the entire house was spotless, comfortable accommodations. We stayed one night and it was perfect for a stopover."
The price is AED 239
AED 466 total
includes taxes & fees
1 May - 2 May
Blue Goose / Brook Road Inn

Look West / Brook Road Inn

10.0 out of 10, Exceptional, (3)
"It was so relaxed and nice. We had a room with our three children. It was lovely. We didn’t take advantage of the kitchen, but it looked really nice."
The price is AED 356
AED 614 total
includes taxes & fees
1 May - 2 May
Look West / Brook Road Inn

Newport Sunshine/Brook Road Inn

9.0 out of 10, Wonderful, (4)
"We stay at the Brook Wood Inn when visiting family in nearby Unity. This was our 2nd stay at the Inn and it is very relaxing place to stay. The common areas and kitchen is great, we always make our own breakfast and have a nice cup of coffee together each morning :)"
The price is AED 316
AED 550 total
includes taxes & fees
1 May - 2 May
Newport Sunshine/Brook Road Inn

Lavender / Brook Road Inn

8.0 out of 10, Very Good, (3)
"I love this place - the only issue was the heater in the room would not regulate - it was a steady 79 degrees no matter how much we tried to lower the thermostat. We followed instructions but we could not lower it"
The price is AED 275
AED 506 total
includes taxes & fees
25 May - 26 May
Lavender / Brook Road Inn

Gunnison Brook / Brook Road Inn

8.0 out of 10, Very Good, (3)
"Beautiful little get away that provided a nice rest while traveling. The inn was charming, very clean and quiet. Highly recommend!!"
The price is AED 334
AED 570 total
includes taxes & fees
1 May - 2 May
Gunnison Brook / Brook Road Inn

Chandler / Brook Road Inn

8.0 out of 10, Very Good, (4)
"Easy process near the slopes."
The price is AED 356
AED 614 total
includes taxes & fees
1 May - 2 May
Chandler / Brook Road Inn

Moss Creek / Brook Road Inn

8.8 out of 10, Excellent, (3)
"You need carpeting upstairs- the amount of stomping around at 530am over the weekend was frustrating. I also understand not serving food right now- however to expect guests to not eat in the comfort of their own rooms and expecting them to eat out in a common area but not serving food is a little hypocritical to be honest. The facility was nice, i liked being able to come and go as i pleased. "
The price is AED 334
AED 570 total
includes taxes & fees
1 May - 2 May
Moss Creek / Brook Road Inn

Victorian Rose / Brook Road Inn

7.0 out of 10, Good, (2)
"Didn't like that no staff was available or reachable! Power out - no response. Check-in problems - no staff or response. Coffee maker quit - nobody to help us or to inform on site in the moment Reservations were a mess due to "responses" from Expedia (our booking service), VRBO, and "Hosteeva" - the last 2 of which we never used! Who is in charge and why are they not there? The system sucks."
The price is AED 316
AED 550 total
includes taxes & fees
1 May - 2 May
Victorian Rose / Brook Road Inn

Salt Ash Inn

3.0 star property
6.0 out of 10, (126)
"Great place, close proximity to Killington. Clean & quiet...Recommend this location."
Salt Ash 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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"This was our second stay at the cozy cottage amd was just as enjoyable as the first time . Glenn and Melanie are very responsive and like to makesure their guests are comfortable and happy . We loved waking up on the lake and enjoyed the back deck and firepit. We look forward to renting here again in the future. P"
Cozy Crescent Cottage

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (103)
"The community, this unit in particular, and its hosts are all spectacular beyond belief. There was one technical/communication glitch that can easily be remedied. Prior communications were encrypted in VRBO platform. When I arrived, I needed to access those in order to refresh my recollection on entry instructions. There's no cellular internet service in the area (need wi-fi connection). Unable to enter the unit, I likewise could not connect to the host-provided wi-fi. I had some of the...
Beautifully renovated with fireplace and coffee bar
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.