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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 168 Vacation Homes in South Windsor with updated reviews, rates, and availability.

Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station
Cozy 2 Bedroom Family Stay
Private kitchen

Cozy 2 Bedroom Family Stay

9.8 out of 10, Exceptional, (7)
"The property was within a few miles to my family who we were visiting. It was very across the street from a very good pub and a couple of minutes to the town’s downtown with several good restaurants to choose from.The apartment was clean with a very comfortable bed and nice furnishings. The kitchen was well equipped with dining and cooking tools. It’s nice to have a good smart tv as well to watch football games. "
Cozy 2 Bedroom Family Stay
PICON COZY
Fridge, microwave, oven, stovetop

PICON COZY

7.8 out of 10, Good, (60)
"Peaceful everything just as listed "
The price is AED 275
AED 625 total
includes taxes & fees
22 Mar - 23 Mar
PICON COZY
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

9.2 out of 10, Wonderful, (11)
"Nice house! Beautiful location only issue let waters run because they ran brown for the start, so don’t turn water on and jump in shower. "
The price is AED 437
AED 1,020 total
includes taxes & fees
13 Mar - 14 Mar
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Outdoor pool

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (6)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Amazing 5-bedroom house in Mansfield
Terrace/patio

Amazing 5-bedroom house in Mansfield

The price is AED 1,025
AED 1,318 total
includes taxes & fees
27 Mar - 28 Mar
Amazing 5-bedroom house in Mansfield
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Bathtub, hair dryer, towels, soap

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

8.8 out of 10, Excellent, (18)
"We had such a wonderful time during our winter stay! The place was super cozy, and the heating made it feel like a warm retreat from the cold outside. We really appreciated the hospitality and can't wait to come back again! "
The price is AED 525
AED 1,129 total
includes taxes & fees
17 Mar - 18 Mar
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Exterior

Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

9.8 out of 10, Exceptional, (115)
"Beautiful house, sitting high and overlooking the Connecticut River. Can't imagine a more beautiful setting. Very large kitchen, great for cooking in with friends. Even has an adjacent helicopter pad (although it's $4k to go from Hartford airport to the house, 1-way!). Had a great time."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (14)
"I had another wonderful stay here at this beautiful property. This is my second of three reviews because I booked them separately before I knew my full travel schedule. The property is exactly as listed and even better. The host does a great job. The home is very comfortable. Despite a massive snowstorm, I was warm and cozy. Snow removal was done and nothing interrupted my stay. The bedrooms, both have very comfortable beds. The shower is terrific with abundant, hot water and pressure.. The...
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Thomas's Cozy Duplex - Centrally Located
Smart TV

Thomas's Cozy Duplex - Centrally Located

8.6 out of 10, Excellent, (10)
"The duplex was clean and quiet. The kitchen was stocked well enough for us to make dinner, although there was no kitchen towel for drying hands and dishes (very minor). Three bedrooms, two with a double/queen, one with a single, and it looked like the couch in the living room was a pull out. Beds were comfortable with plenty of bedding. Wi-fi worked well. Couldn't ask for anything more. I would stay here again if in the area. "
The price is AED 404
AED 975 total
includes taxes & fees
13 Mar - 14 Mar
Thomas's Cozy Duplex - Centrally Located
The Skyway
Private kitchen

The Skyway

10.0 out of 10, Exceptional, (2)
"Very well staged. Smart TV’s in every room. Quiet, safe area. Comfortable bed. It was perfect for my short stay"
The price is AED 342
AED 1,151 total
includes taxes & fees
17 Mar - 18 Mar
The Skyway
NEW-Another Fun Downtown Location 1st floor
Interior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (10)
"Can’t beat proximity to downtown and other CT locations.Unfortunately we were hit with icy conditions so we could not enjoy all it has to offer. Owner checked in on us and kept driveway safe and clear. We really appreciated his hospitality.The rental was well equipped with everything you need. I LOVED the sunny kitchen to enjoy my morning coffee.We’ll definitely come back when it is warmer!"
NEW-Another Fun Downtown Location 1st floor
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Property grounds

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (54)
"Love this place for popping in and cooking homemade meals for my daughter and her teammates "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (3)
"We came to the area for a long weekend event at Wesleyan University. I had never booked through VRBO and was not familiar with the process. From my first communication with Gilbert I felt like I was going to visit family. He was amazing to communicate with provided information about the area and the process and was super accommodating when he learned our flight was arriving early. From the moment we stepped through the door we knew our stay would be special. The home is beautiful, beds...
The price is AED 367
AED 686 total
includes taxes & fees
26 Mar - 27 Mar
Family Stays: Middletown, CT
WeHa Oak Haven
Private kitchen

WeHa Oak Haven

10.0 out of 10, Exceptional, (3)
"The property is a townhome that is very easy to find and very accessible to the main highway to get anywhere you need easily. It is also located near a couple very good restaurants within walking distance that I would highly suggest, Iron Works and Effies Diner. It was perfect for the two of us for the week. Thank you!"
WeHa Oak Haven
Charming 3-bedroom house with WiFi, Workspace, Pet-Friendly in Manchester
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, Workspace, Pet-Friendly in Manchester

Charming 3-bedroom house with WiFi, Workspace, Pet-Friendly in Manchester
Amazing lake house with everything you need!
Property grounds

Amazing lake house with everything you need!

10.0 out of 10, Exceptional, (6)
"I enjoyed my stay at Jason‘s cottage. The neighborhood was quiet in the winter, with only a handful of neighbors. Jason was great, communicating, and helpful when I accidentally left a couple things behind."
Amazing lake house with everything you need!
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Fridge, microwave, oven, stovetop

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Linny's Updated Lakeview Cottage - Cozy & Modern
Fridge, microwave, oven, stovetop

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (57)
"More than expected, owner pays attention to detail, many amenities, spotless. All the comforts of home. Owner very prompt to answer any questions. Will definitely be booking this againRobbin and Rich Willis"
Linny's Updated Lakeview Cottage - Cozy & Modern
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Interior

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

9.8 out of 10, Exceptional, (21)
"Great place for family camping in summer with a beautiful lake nearby. The winter experience is quite different but still provides a special experience due to the old and nostalgic settings. Nostalgic old setting. but"
The price is AED 496
AED 1,091 total
includes taxes & fees
18 Mar - 19 Mar
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
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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Other property types in South Windsor

Cozy 2BR Retreat Near Downtown Springfield
Fridge, microwave, oven, stovetop

Cozy 2BR Retreat Near Downtown Springfield

Cozy 2BR Retreat Near Downtown Springfield
Treehouse - Countryside - Farm Animals - Fire Pit
Property grounds

Treehouse - Countryside - Farm Animals - Fire Pit

9.6 out of 10, Exceptional, (24)
"Such a magical idea, something I knew my wife would appreciate and the treehouse didn't disappoint! - In the dead of winter, the gas fireplace not only was fantastic ambiance, but kept both floors extremely cozy - The treehouse itself was very clean and everything worked as expected- Perfect environment for snuggling, reading a book, or taking time to communicate with each other- Online check-in, check-out was simple- The grounds looked wonderful, although we where passing through and didn't...
The price is AED 364
AED 913 total
includes taxes & fees
17 Mar - 18 Mar
Treehouse - Countryside - Farm Animals - Fire Pit
Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station
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.