South Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for South Windsor vacation rentals

Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
8.8 out of 10, Excellent, (48)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
The price is ￥15,501
￥39,528 total
includes taxes & fees
Dec 18 - Dec 19
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is ￥15,501
￥38,753 total
includes taxes & fees
Dec 18 - Dec 19
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Cottage in Stafford

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
9.6 out of 10, Exceptional, (30)
"Great host- fun property!"
United States
Mary F.
The price is ￥20,120
￥50,029 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is ￥17,981
￥47,146 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Soothing 2-bedroom lower-level apartment in Berlin
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Vacation Home in Coventry Lake

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
9.8 out of 10, Exceptional, (34)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is ￥18,446
￥43,379 total
includes taxes & fees
Dec 18 - Dec 19
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Outdoor dining
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Vacation Home in Ashford

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
9.4 out of 10, Exceptional, (19)
"We had a nice getaway after a tour of our alma mater, UCONN. This welcoming and very well decorated home gave us a nice place to rest and connect after our busy day."
United States
Andrea F.
The price is ￥25,577
￥52,975 total
includes taxes & fees
Dec 21 - Dec 22
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Fridge, microwave, stovetop, coffee/tea maker
West Hartford Affordable, NEW, & Parking Included

Apartment in West Hartford

West Hartford Affordable, NEW, & Parking Included
2.0 star property
10.0 out of 10, Exceptional, (1)
West Hartford Affordable, NEW, & Parking Included
Fridge, microwave, oven, stovetop
Modern & Cozy Cape | 4 Bedroom House | Central Location

Vacation Home in Manchester Center

Modern & Cozy Cape | 4 Bedroom House | Central Location
10.0 out of 10, Exceptional, (5)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is ￥16,896
￥40,512 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Modern & Cozy Cape | 4 Bedroom House | Central Location
Exterior
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Cabin in Ashford

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
9.2 out of 10, Wonderful, (25)
"Hosted a bachelorette trip at this property and it was fantastic. The kayaks and paddle boards provided plenty to do along with a firepit to sit around at night. The house was cozy with plenty of space to sleep 5. Had a great time! "
United States
Renee J.
The price is ￥18,418
￥43,313 total
includes taxes & fees
Dec 18 - Dec 19
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Interior
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Apartment in Willington

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
9.6 out of 10, Exceptional, (11)
"Very nice country stay. "
United States
michael C.
The price is ￥15,036
￥39,148 total
includes taxes & fees
Dec 28 - Dec 29
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Dining
The Serene Skyway Retreat

Vacation Home in Windsor Locks

The Serene Skyway Retreat
9.0 out of 10, Wonderful, (12)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is ￥12,091
￥42,419 total
includes taxes & fees
Dec 22 - Dec 23
The Serene Skyway Retreat
Property grounds
Humble Abode #2

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥18,572
￥24,453 total
includes taxes & fees
Dec 30 - Dec 31
Humble Abode #2
Spa
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Apartment in East Windsor

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
2.0 star property
9.8 out of 10, Exceptional, (18)
"Great stay! Very clean and easily accessible"
United States
Nick T.
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Vacation Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is ￥17,412
￥37,359 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Fridge, microwave, oven, stovetop
#23 *COMFORT & LUXURY* 3 BR/2 BA House

Apartment in Southington

#23 *COMFORT & LUXURY* 3 BR/2 BA House
9.8 out of 10, Exceptional, (8)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Property grounds
Treehouse - Countryside - Farm Animals - Fire Pit

Cabin in Willington

Treehouse - Countryside - Farm Animals - Fire Pit
9.4 out of 10, Exceptional, (28)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is ￥20,461
￥46,317 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Treehouse - Countryside - Farm Animals - Fire Pit
Fridge, stovetop, coffee/tea maker, toaster
Charming New England Tiny Home in Cromwell, CT

Apartment in Main Street Historic District

Charming New England Tiny Home in Cromwell, CT
10.0 out of 10, Exceptional, (1)
"It was the perfect escape- close enough to home but just far enough to feel like a vacation, the whole process was 10 out of 10 and def worth a 2nd stay!"
United States
Amanda G.
Charming New England Tiny Home in Cromwell, CT
Exterior
The Blue Back Bungalow

Apartment in West Hartford

The Blue Back Bungalow
2.0 star property
9.4 out of 10, Exceptional, (17)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
The price is ￥13,775
￥49,991 total
includes taxes & fees
Dec 30 - Dec 31
The Blue Back Bungalow
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Apartment in Manchester

Central Chic Pad - with Free Parking, Heat & AC
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is ￥13,548
￥32,786 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Central Chic Pad - with Free Parking, Heat & AC
Outdoor dining
The Historic Hideaway

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is ￥8,526
￥37,783 total
includes taxes & fees
Dec 18 - Dec 19
The Historic Hideaway
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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Top South Windsor Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Clean room. Great location. Very nice staff."
William 2-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG

Find out more about South Windsor

Search for holiday rentals in South Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in South Windsor using one of the methods below:

  • View our selection of featured holiday rentals in South Windsor
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  • Enter your travel dates to view the best deals on holiday rentals in South Windsor while they last

Look no further and take a look at our great range of rental properties in South Windsor!

Frequently asked questions

Are there vacation rentals in South Windsor?

Yes, we offer vacation rentals in South Windsor near Nomads Adventure Quest, or you can choose a secluded option if you're looking for extra privacy while you relax. South Windsor is known for its shopping and golf courses. Make sure you have time to check out the restaurants while you're in the area.

What's the top vacation rental in South Windsor?

Private Apartment in Berlin: This vacation home rental outside of South Windsor is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in South Windsor?

Connecticut River and South Windsor Bark Park are a couple of scenic spots to enjoy the outdoors, whereas Wood Memorial Library & Museum is one of the cultural attractions. Other places in town to visit include Nomads Adventure Quest and Promenade Shops at Evergreen Walk.

What’s a vacation rental in South Windsor like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in South Windsor. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family trip.