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Compare 213 Vacation Homes in Windsor with updated reviews, rates, and availability.

Comfortable New Decor in Living Room Equipped w Smart TV and Deck

"It was an amazing stay. The host was very proactive and helpful. "

AED 1,969 total

includes taxes & fees

18 Nov - 19 Nov

"Beautiful, spacious house in a great location!"

"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."

"One of the best properties i've ever stayed at "

AED 751 total

includes taxes & fees

18 Nov - 19 Nov

The house was originally built in 1864 and completely updated in 2009

"We stayed at Chris' mansion for my wedding this past weekend and it was everything I expected and more. Although it isn't a full service venue, the owner Chris was sooooo helpful in getting everything we needed for our wedding. He owns a restaurant as well and was able to provide all of our appetizers, servers and bartenders! We even had our rehearsal dinner at his bar down the street called Jax on Tap. The bartenders were absolutely amazing and made us feel so welcome. They even made a sign...

Breakfast Nook - wake up to the best sunshine ever!

"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "

"We really enjoyed our stay at Julie’s home. We will definitely to look to stay here again the next time we visit the area. Highly recommended! "

"Very clean and nicely decorated. Comfortable vibe. Came to relax and enjoy the fall colors. It looks bigger in the pictures, but was plenty big for the 4 of us. Having laundry was a plus, and enjoyed the ping pong table Loved the duvet covers…so soft. Upstairs bathroom could use a mirror in a better place, as blow drying hair and putting on makeup would be difficult, but just didn’t bother. Hope to go again next fall. "

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Other property types in Windsor

"Love staying here "

AED 717 total

includes taxes & fees

16 Nov - 17 Nov

"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "

AED 600 total

includes taxes & fees

16 Nov - 17 Nov

"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...

Recent reviews of Windsor hotels

5/5 Excellent

Black Swan

"We booked this place for a one-night stay to check out the Berkshires. This was pretty much centrally located from everything we wanted to visit. We chose this place for the country feel rather than the big city type hotels. The place was a little outdated but had the more of a home feel. There is some updating due there, but it wasn't a disappointment. We will book again when we visit the area to go hiking. Plus, the lake view was ok, and the water looked very clean. I will say this is an excellent spot if you're an outdoor person for fishing. Kayaking etc. "

A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection

Posted 2 days ago