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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 199 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, (10)
"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
PICON COZY
Fridge, microwave, oven, stovetop

PICON COZY

7.6 out of 10, Good, (64)
"Picon Cozy was a great place to rest our weary heads. The neighborhood was quiet and the lodging/amenities met our needs very nicely. We'll definitely consider this place for future visits to the Springfield area 😊."
The price is AED 275
AED 625 total
includes taxes & fees
9 May - 10 May
PICON COZY
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, (15)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Thomas's Cozy Duplex - Centrally Located
Smart TV

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very Good, (11)
"Quiet and comfy "
Thomas's Cozy Duplex - Centrally Located
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, (55)
"We had a lovely time there. The place was super well equipped with all the things you might need, beautifully maintained and peaceful. The access to the lake was great and we used the fire pit outside. Even though it was winter, it was a lovely view and great place to enjoy non screen time with family. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Grammy's Lake House w/ Private Waterfront Access
Interior

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (12)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access
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, (7)
"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
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!! "
The price is AED 1,440
AED 3,046 total
includes taxes & fees
20 May - 21 May
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
WeHa Oak Haven
Private kitchen

WeHa Oak Haven

10.0 out of 10, Exceptional, (5)
"Lovely property in a great area of West Hartford. Will definitely stay again!"
WeHa Oak Haven
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (6)
"Our experience with this facility, from online service to exiting the residence, was the most pleasurable experience, for staying in accommodations when traveling!!The owner was a complete gentleman and it was absolutely wonderful experience to meet and talk with him."
Family Stays: Middletown, CT
Amazing lake house with everything you need!
Property grounds

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (9)
"Everything was wonderful and very convenient "
Amazing lake house with everything you need!
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Outdoor dining

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

9.2 out of 10, Wonderful, (12)
"Everything was great, and plenty of space for our group of 5 adults and one toddler. Communication with the host was very easy, and everything was in place that we needed. There were many touches that make it clear they want you to feel comfortable and at home. Looking forward to visiting again in the summer to take advantage of the lake"
The price is AED 514
AED 1,123 total
includes taxes & fees
20 May - 21 May
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Charming Farmhouse w/ Pool & Fishing Pond!
Fridge, microwave, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (9)
"Very classy, unique, well taken care of home. I would highly recommend this for anyone."
Charming Farmhouse w/ Pool & Fishing Pond!
Cozy 4 Bedroom West Hartford House
Smart TV, fireplace

Cozy 4 Bedroom West Hartford House

2.0 star property
9.0 out of 10, Wonderful, (4)
"This was the best property for our large family. The host was very attentive to our family. Thank again for everything."
Cozy 4 Bedroom West Hartford House
Cozy 2 Bedroom Family Stay
Private kitchen

Cozy 2 Bedroom Family Stay

9.8 out of 10, Exceptional, (8)
"We had a great stay in Manchester! Quick walk to stores, restaurants, and Main St Manchester. The apartment was clean and spacious. Would definitely recommend & stay here again!"
Cozy 2 Bedroom Family Stay
Upscaled Quiet Neighborhood- Modern 3 BDRM
Fridge, microwave, oven, stovetop

Upscaled Quiet Neighborhood- Modern 3 BDRM

10.0 out of 10, Exceptional, (24)
"Nice place to stay"
Upscaled Quiet Neighborhood- Modern 3 BDRM
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Bathtub, hair dryer, towels, soap

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

9.0 out of 10, Wonderful, (19)
"We stayed it town to visit local family members. Accommodations were cleanly & cozy. Although we stayed in January, I can see this being a wonderful place for a small family to enjoy a lovely summer holiday on the lake. Owner was very friendly and easy to communicate with."
The price is AED 566
AED 1,190 total
includes taxes & fees
8 May - 9 May
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AED 459
AED 1,410 total
includes taxes & fees
7 May - 8 May
Blue Back Bungalow
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, (116)
"Property was as described, perfect stay, beautiful home and perfect view. Had everything you could ever want and owner was very accommodating to our dogs."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (31)
"It was nice stay!"
The price is AED 680
AED 1,167 total
includes taxes & fees
5 May - 6 May
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

9.8 out of 10, Exceptional, (11)
"Just a nice lake house!!"
The price is AED 551
AED 1,297 total
includes taxes & fees
19 May - 20 May
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (15)
"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."
The price is AED 621
AED 862 total
includes taxes & fees
5 May - 6 May
Lux Boutique Large Private LOFT Pratt St Hartford
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AED 459
AED 1,410 total
includes taxes & fees
7 May - 8 May
Blue Back Bungalow
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.