A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Windsor vacation rentals

Dining

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 reviews)
"Everything was seamless - we enjoyed the location close to downtown hartford and six flags. the listing was clean and accurate and the beds were comfortable."
United States
AJ P.
The price is ￥51,745
￥113,611 total
includes taxes & fees
Sep 1 - Sep 2
Spacious Yard w/ Gazebo: Charming Windsor Retreat
Smart TV

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
The price is ￥16,052
￥21,645 total
includes taxes & fees
Aug 17 - Aug 18
Entire guest suite in South Windsor, Connecticut
Coffee/tea maker, fridge, microwave, stovetop

3. Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
East Windsor
9.8 out of 10, Exceptional, (27 reviews)
"I would absolutely stay here again. It's perfectly located for seeing a show at Broad Brook Opera House. Parking and check in couldn't be easier. The room has everything you need for a very comfortable stay."
United States
Anthony
The price is ￥21,212
￥27,579 total
includes taxes & fees
Aug 23 - Aug 24
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Coffee/tea maker, fridge, microwave, oven

4. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
9.8 out of 10, Exceptional, (10 reviews)
"Super easy effective rental. Everything was clean and meet everyone one of our needs!"
United States
Matthew R.
The price is ￥29,812
￥71,548 total
includes taxes & fees
Aug 25 - Aug 26
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Property grounds

5. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥19,906
￥26,077 total
includes taxes & fees
Aug 17 - Aug 18
Humble Abode #2
Property grounds

6. Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
Manchester Center
10.0 out of 10, Exceptional, (9 reviews)
"Nice private place to stay."
United States
Brian A.
The price is ￥20,509
￥26,741 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
3 bedrooms, WiFi (free)

7. Location, is the key for this 3 bedroom!

Location, is the key for this 3 bedroom!
Frog Hollow
9.6 out of 10, Exceptional, (7 reviews)
"It was nice and close to where we had a wedding. Plenty of room for us all. Host was very easy to contact. "
United States
Shawn R.
The price is ￥33,251
￥77,972 total
includes taxes & fees
Sep 10 - Sep 11
Location, is the key for this 3 bedroom!
Interior

8. West Hartford Center: Charming New England Apt

West Hartford Center: Charming New England Apt
West Hartford
10.0 out of 10, Exceptional, (8 reviews)
"Highly recommend! The apartment is bright and clean, equipped with everything we needed for a short stay. Walking distance to West Hartford, which offers great restaurant options. "
United States
Evan B.
The price is ￥42,998
￥80,677 total
includes taxes & fees
Aug 17 - Aug 18
West Hartford Center: Charming New England Apt
Smart TV, offices

9. Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
The price is ￥17,780
￥38,748 total
includes taxes & fees
Aug 16 - Aug 17
Premier League Pad - with Free Parking, Heat & AC
Smart TV, fireplace

10. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (16 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is ￥20,066
￥54,607 total
includes taxes & fees
Aug 12 - Aug 13
The Serene Skyway Retreat
TV, books

11. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
The Game House Arcade – West Hartford
1 bedroom, desk, iron/ironing board, WiFi (free)

12. Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester

Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (14 reviews)
"Great place"
United States
Jason
The price is ￥19,878
￥33,903 total
includes taxes & fees
Aug 13 - Aug 14
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
Interior

13. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
Linny's - Private Dock - Lake Access - Firepit
Smart TV, offices

14. Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (1 review)
"Perfect place for a quick stay"
United States
phillip s.
The price is ￥13,735
￥33,791 total
includes taxes & fees
Aug 30 - Aug 31
Crested One Place - with Free Parking, Heat & AC
Interior

15. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is ￥20,703
￥47,377 total
includes taxes & fees
Aug 31 - Sep 1
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV, offices, computer monitors

16. TruStay in Central CT

TruStay in Central CT
Manchester
10.0 out of 10, Exceptional, (1 review)
"The apartment was immaculate. Everything new, Very comfortable."
United States
Maxine L.
The price is ￥16,510
￥37,287 total
includes taxes & fees
Aug 18 - Aug 19
TruStay in Central CT
Smart TV, offices, computer monitors

17. Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is ￥13,607
￥33,318 total
includes taxes & fees
Sep 1 - Sep 2
Central Chic Pad - with Free Parking, Heat & AC
Terrace/patio

18. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (19 reviews)
"The bungalow is in a great location - close to I84 and West Hartford center. The kitchen had a lot of great appliances to make cooking easy. The coffee pot was a Keurig/carafe combo - which we really liked. We enjoyed drinking our morning coffee on the front porch. We would definitely stay her again!"
United States
Ben
The price is ￥15,776
￥53,851 total
includes taxes & fees
Aug 12 - Aug 13
The Blue Back Bungalow
Living area

19. Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
Manchester
The price is ￥20,390
￥42,696 total
includes taxes & fees
Aug 13 - Aug 14
Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
TV, fireplace

20. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very Good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is ￥14,755
￥63,212 total
includes taxes & fees
Aug 12 - Aug 13
Willow Haven 2BR Cozy Retreat, Close to Hartford
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 Windsor Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Room was great"
Freddie 1-night trip
Posted 1 hour ago
Holiday Inn Express Southington by IHG

Find out more about Windsor

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

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals in Windsor close to Windsor Arts Center, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What's the top vacation rental that Windsor has to offer?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This highly rated vacation home rental in Windsor has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Windsor?

Expedia has 7 vacation rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Historical Society and Vintage Radio and Communications Museum of Connecticut, whereas Keney Park and Northwest Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Windsor Arts Center and Loomis Chaffee School.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.