Holiday houses in South Windsor

Find and book unique accommodation on Airbnb

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Popular amenities for South Windsor holiday rentals

Stay near South Windsor's top sights

The Promenade Shops at Evergreen Walk15 locals recommend
The Shoppes at Buckland Hills7 locals recommend
Buckland Mall and Pavillon Dr station11 locals recommend
Rein's New York Style Deli4 locals recommend
Buckland Hills 18 and IMAX8 locals recommend
The Mill on the River3 locals recommend

Other great holiday rentals in South Windsor

Top Guest favourite
Home in Great Barrington
5 out of 5 average rating, 13 reviews

Great 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 reviews

Pet 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 reviews

Summer 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 reviews

State 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 reviews

Lovely 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 reviews

Beachfront 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 reviews

Great 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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