
Holiday houses in South Windsor
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Top-rated holiday rentals in South Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in South Windsor
Top Guest favourite

Home in Great Barrington
5 out of 5 average rating, 13 reviewsGreat Barrington Ranch. Sleeps 10,Hot Tub, 5 acres
JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Top Guest favourite

Cottage in Guilford
4.99 out of 5 average rating, 136 reviews"Red House on the Knoll" at Indian Cove
MaryRating, 5 stars3 weeks ago
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!
Top Guest favourite

Bungalow in Old Lyme
4.94 out of 5 average rating, 308 reviewsPet Friendly Bungalow!!!
AlexanderRating, 5 stars1 week ago
Our stay at June’s bungalow was the perfect weekend escape we needed to reset and recharge. From the start, June was incredibly warm, kind, and attentive—she truly went above and beyond to make sure we felt welcome. Communication was seamless, and her local recommendations were spot-on. The bungalow itself is charming, cozy, and thoughtfully stocked with everything you could possibly need. It’s also wonderfully pet-friendly—our dog had the best time exploring and relaxing right alongside us. We couldn’t have asked for a better experience and would wholeheartedly recommend June’s place to anyone looking for a peaceful and pet-friendly getaway.
Superhost

Home in Waterford
4.94 out of 5 average rating, 18 reviewsSummer Beach Cottage Harknes, Ocean Beach N
JenniferRating, 5 stars8 months ago
It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.
Superhost

Home in Cornwall
4.83 out of 5 average rating, 98 reviewsState Forest Getaway
MattRating, 5 stars5 days ago
Such a gracious host, easy and everything was flawless. The space is just magical, so relaxing, and the surrounding areas are beautiful. Feels like home from the minute you walk in.
Guest favourite

Cottage in Great Barrington
4.95 out of 5 average rating, 22 reviewsLovely in-town home with screen porch & sun deck
SarahRating, 5 stars4 months ago
We loved loved loved the cottage! It’s the best decorated air Bnb we have ever stayed in. Like being at a wonderful cousin’s home with books and gorgeous dishes and bikes and quilts and good books and window seats everywhere you look. And great art, painted (I think) by the owner? The neighbors are so friendly and the town is fantastic. Cozy, warm, delightful.
Guest favourite

Home in Woodmont
4.98 out of 5 average rating, 43 reviewsBeachfront paradise- come, stay, relax!
TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top Guest favourite

Home in Old Saybrook
5 out of 5 average rating, 50 reviewsGreat Hammcock Getaway, Nearby beaches, Hot tub
ChrisRating, 5 stars2 days ago
My family and I enjoyed our stay. The accommodation was well appointed with all ameneties and cooking utilities to provide for a wonderful stay. We enjoyed the private back yard area and porch for dinners outside. Harvey's Beach is a walkable and we enjoyed some beach time there. Irina is a very responsive host and provided some great local tips on restaruants and places to visit. We would recommend this spot for folks looking for a location both close to beaches and town area. The accommodation is welcoming and very suitable for families or groups.
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- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Six Flags New England
- TPC River Highlands
- Quotonset Beach
- Giants Neck Beach
- Woodmont Beach
- Clinton Town Beach
- Shennecossett Beach
- Attawan Beach
- Bushnell Park
- Anchor Beach
- Grove Beach
- Waterford Beach Park
- Groton Long Point Main Beach
- Groton Long Point South Beach
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Burwells Beach
- Oak Street Beach
- Silver Sands Beach
- Garvan Point Beach
- Barbara Pine Memorial Beach