South Windsor Vacation Rentals

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Check prices for these dates

Tonight
Dec 17 - Dec 18
Tomorrow
Dec 18 - Dec 19
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for South Windsor vacation rentals

Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Apartment in Downtown Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
8.6 out of 10, Excellent, (24)
"Great stay"
United States
Josh H.
The price is ￥15,477
￥23,564 total
includes taxes & fees
Dec 18 - Dec 19
Lux Boutique Large Private LOFT Pratt St Hartford
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
￥38,133 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Interior
Experience Downtown Hartford near XL Center

Apartment in Downtown Hartford

Experience Downtown Hartford near XL Center
6.6 out of 10, (7)
"Nice place, good location. "
United States
Lacey A.
The price is ￥15,477
￥23,564 total
includes taxes & fees
Dec 21 - Dec 22
Experience Downtown Hartford near XL Center
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Vacation Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is ￥18,108
￥48,915 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Apartment in Berlin
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 ￥20,739
￥46,292 total
includes taxes & fees
Dec 30 - Dec 31
Treehouse - Countryside - Farm Animals - Fire Pit
Full-size fridge, microwave, oven, dishwasher
Newly Renovated 2 floor Getaway

Apartment in Forest Park

Newly Renovated 2 floor Getaway
3.5 star property
The price is ￥61,502
￥92,992 total
includes taxes & fees
Dec 29 - Dec 30
Newly Renovated 2 floor Getaway
Microwave
Cozy apartment in charming Hartford with AC, WiFi

Apartment in Downtown Hartford

Cozy apartment in charming Hartford with AC, WiFi
8.8 out of 10, Excellent, (9)
"Very nice for one night"
United States
Jack
The price is ￥15,477
￥23,564 total
includes taxes & fees
Dec 30 - Dec 31
Cozy apartment in charming Hartford with AC, WiFi
3 bedrooms, iron/ironing board, WiFi, bed sheets
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

Vacation Home in Washington Street Historic District

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
6.6 out of 10, (4)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
United States
Jenn U.
The price is ￥23,216
￥29,794 total
includes taxes & fees
Dec 28 - Dec 29
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
HOMEY HOMEY

Apartment in Sixteen Acres

HOMEY HOMEY
2.8 out of 10, (5)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
United States
Erin N.
The price is ￥11,143
￥25,811 total
includes taxes & fees
Dec 21 - Dec 22
HOMEY HOMEY
Fridge, microwave, oven, stovetop
Charming 3-Bedroom Home with Modern Comforts in West Hartford

Vacation Home in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
2.0 star property
8.6 out of 10, Excellent, (9)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is ￥21,281
￥47,535 total
includes taxes & fees
Dec 18 - Dec 19
Charming 3-Bedroom Home with Modern Comforts in West Hartford
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
￥50,494 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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 23 - Dec 24
Humble Abode #2
Terrace/patio
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Vacation Home in Barkhamsted

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
10.0 out of 10, Exceptional, (4)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Spain
Heather A.
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Fridge, microwave, oven, stovetop
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

Vacation Home in Windham

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
9.8 out of 10, Exceptional, (8)
"Great house for family visit with our USCG cadet. The owners were very flexible and responsive to our needs. The property was clean and spacious we will use again! "
United States
Mark M.
The price is ￥25,577
￥88,162 total
includes taxes & fees
Dec 22 - Dec 23
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Interior
Conference Room Rental no sleeping arrangements

Apartment in Main Street Historic District

Conference Room Rental no sleeping arrangements
The price is ￥111,434
￥144,090 total
includes taxes & fees
Dec 21 - Dec 22
Conference Room Rental no sleeping arrangements
Dining
Amazing lake house with everything you need!

Vacation Home in Ashford

Amazing lake house with everything you need!
9.8 out of 10, Exceptional, (22)
"Great time, lovely location, easy to access and beautiful lake!"
United States
Sam L.
Amazing lake house with everything you need!
Smart TV
PICON COZY

Vacation Home in Sixteen Acres

PICON COZY
7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
United States
Linda W.
The price is ￥11,763
￥26,514 total
includes taxes & fees
Dec 26 - Dec 27
PICON COZY
Fridge, microwave, oven, stovetop
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Apartment in Forest Park

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
9.0 out of 10, Wonderful, (28)
"This home was great. It had everything our large group needed and was as advertised. The owner was great to communicate with. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is ￥40,496
￥81,290 total
includes taxes & fees
Dec 18 - Dec 19
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Apartment in Downtown Hartford

Totally Private Cozy studio in awesome Hartford with WiFi, AC
8.6 out of 10, Excellent, (11)
"Great location, very nice and clean. "
United States
Manuel M.
The price is ￥15,477
￥23,564 total
includes taxes & fees
Dec 22 - Dec 23
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Vacation Home in Bloomfield

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
2.0 star property
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is ￥47,669
￥110,304 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
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:

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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.