Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Becket

4.94 out of 5 average rating, 197 reviews

SarahRating, 5 stars1 week ago

We had a wonderful stay at Loksze’s beautiful home! The home was exactly as described; clean, comfortable, and well-stocked with everything we needed. The location was perfect, making it easy to explore the area, and the peaceful atmosphere made for a relaxing getaway. We would absolutely stay here again and highly recommend this place to anyone looking for a great stay in a beautiful location!

Guest favourite

Apartment in Stockbridge

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

ReganRating, 5 stars3 months ago

Theresa’s beautiful Norman Rockwell studio was so much better than I could have imagined! She was so thoughtful from start to finish with clear and easy communication about everything. Parking was very easy and you will clearly have a space right behind the building. The large picture window in the middle of the living room with a Christmas tree in the center was so lovely and heart warming! Very quiet yet steps from shopping and restaurants (the best breakfast in town can be had at Main Street Cafe downstairs!) I would highly recommend this charming apartment for anyone wanting a charming experience in Stockbridge. 10 out of 10!

Top Guest favourite

Home in Canton

4.99 out of 5 average rating, 109 reviews

Best River View, on Rail Trail in Collinsville!

AmyRating, 5 stars4 weeks ago

I reached out to Carol after we had been in a horrible Air B&B situation in a near by town.. She accommodated us on the very day we needed to check in. Her place is stunning! And very charming. The views are to die for. We had everything we needed. I would definitely stay there again and would highly recommend her place. Also, snacks and essentials were left for us and plenty of coffee! I will never forget the beautiful view sitting in the family room overlooking lake.

Top Guest favourite

Home in Brimfield

4.94 out of 5 average rating, 163 reviews

Brimfield Lakeside Home Away from Home

MaureenRating, 5 stars1 week ago

My sister and I spent a few relaxing days at Shannon's home. We had a wonderful time! It's in a great location- close enough to town to see the sights and go to restaurants, but also far enough away to be so peaceful and private. We booked it because we love being near water, and the house didn't disappoint. We loved the view. It was a bit windy and cool while we were there, but we were able to sit outside several times by the lake and use the fire pit. We also enjoyed watching and listening to the many birds around the house. The house itself was warm and comfortable and had everything we needed. We were happy to meet Shannon when we checked in. She answered questions we had and made recommendations based on our conversation. Thanks Shannon for having us, and we would love to come back sometime to your lovely home! Highly recommend!!

Holiday rentals for every style

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Popular amenities for Windsor holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Windsor's top sights

Price Chopper15 locals recommend

Revolutions Bowling and Lounge7 locals recommend

University of Hartford5 locals recommend

Tunxis Grill & Pizzeria5 locals recommend

Thomas Hooker Brewery5 locals recommend

The Children's Museum5 locals recommend

Other great holiday rentals in Windsor

Guest favourite

Guesthouse in Southbury

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars3 months ago

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

Top Guest favourite

Home in Granby

5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars1 week ago

We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!

Top Guest favourite

Home in Andover

4.98 out of 5 average rating, 56 reviews

Spacious Classic Lakefront Home with jet tub

JeffreyRating, 5 stars3 months ago

The house felt like coming home. Everything you need was provided. The location is beautiful as is the surrounding area. We needed proximity to family and this was a perfect spot. All the amenities in the home were available and perfect for a weeklong stay. Thank you for a great stay!

Superhost

Apartment in Chester

4.77 out of 5 average rating, 197 reviews

Quiet getaway in the Berkshires

MarkRating, 5 stars2 weeks ago

The place is a large upstairs apartment built into a single family home with a business on the first floor. Very Chester. Comfortable and warm. Everything was and felt clean, no worries there.

Superhost

Cabin in Lebanon

4.86 out of 5 average rating, 14 reviews

Casa Lago

JillianRating, 5 stars7 months ago

I didnt want to leave this little cabin in the woods. It felt rustic but had all the modern amenities you would expect in a home. From the rocking chairs on the porch to the comfy beds, there is nothing I could complain about, even if I tried. Marilyn gave excellent suggestions of places to eat and local current events. We left with fall apples, bellies full of clam chowder, and gigantic smiles!!! We have already started planning our return!

Guest favourite

Home in Otis

4.92 out of 5 average rating, 153 reviews

The Pinnacle House at Otis Ridge Ski Area!

AmyRating, 5 stars2 months ago

Welcoming, tidy and clean home. Fully functional and amenable to families with young children. A perfect winter getaway spot given its proximity to Otis Ridge. Extremely easy to ski in and ski out. Mary Kay is a lovely host- extremely responsive, helpful and flexible.

Top Guest favourite

Cabin in Sandisfield

4.99 out of 5 average rating, 103 reviews

Berkshires Cabin in Woods with Mountain Views

KelseyRating, 5 stars2 months ago

We were so glad to be back at Mike and Lianne's cozy, beautiful place. The house is clean, comfortable, and well-equipped, the surrounding are lovely, and there's lots of fun winter activities close by. We hope to return soon!

Superhost