A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windsor vacation rentals

A spacious kitchen with wooden cabinets, a large island, and a dining area with chairs and a rug.

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 reviews)
"The place is easy to locate. It is as beautiful as the photo. Clean and spacious.I definitely would stay there again."
United States
Delores N.
The price is ￥52,070
￥114,483 total
includes taxes & fees
Sep 30 - Oct 1
Spacious Yard w/ Gazebo: Charming Windsor Retreat
A modern living room with a sofa, a coffee table, and a rug.

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is ￥13,716
￥18,948 total
includes taxes & fees
Sep 29 - Sep 30
Entire guest suite in South Windsor, Connecticut
A living room with a dining area, a TV, and a large window with a view of buildings.

3. 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 ￥13,692
￥34,479 total
includes taxes & fees
Oct 5 - Oct 6
Central Chic Pad - with Free Parking, Heat & AC
A blue sofa with plaid pillows, a glass coffee table with a white flower centerpiece, and two potted plants.

4. 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 ￥17,725
￥38,944 total
includes taxes & fees
Sep 27 - Sep 28
Premier League Pad - with Free Parking, Heat & AC
A bedroom with a bed, two bedside lamps, a nightstand, a dresser, and artwork on the wall.

5. 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, (18 reviews)
"Great place"
United States
Jason
The price is ￥19,817
￥33,170 total
includes taxes & fees
Sep 27 - Sep 28
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

6. 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 ￥13,692
￥34,479 total
includes taxes & fees
Oct 4 - Oct 5
Crested One Place - with Free Parking, Heat & AC
A living room with a TV, sofas, armchairs, and a fireplace.

7. 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 ￥14,708
￥70,480 total
includes taxes & fees
Sep 30 - Oct 1
Willow Haven 2BR Cozy Retreat, Close to Hartford
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

8. 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 ￥21,862
￥46,374 total
includes taxes & fees
Oct 13 - Oct 14
Modern & Cozy Cape | 4 Bedroom House | Central Location
A living room with a sectional sofa, a coffee table, a dining table with chairs, and a window with curtains.

9. 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 ￥16,788
￥37,086 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
A wooden deck with a staircase leading to a covered area with chairs.

10. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (5 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥18,874
￥24,851 total
includes taxes & fees
Sep 28 - Sep 29
Humble Abode #2
A kitchen with wooden shelves, a toaster, and a sink.

11. 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
9.6 out of 10, Exceptional, (28 reviews)
"Great stay and location for a single traveler with a dog! Owners were good communicators. Would stay again!"
United States
Nicole G.
The price is ￥20,950
￥27,238 total
includes taxes & fees
Oct 10 - Oct 11
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

12. 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 ￥19,844
￥51,069 total
includes taxes & fees
Oct 5 - Oct 6
The Serene Skyway Retreat
A bedroom with a bed, bedside tables, a nightstand, and a patterned rug.

13. Premium Enjoyable 1-bedroom apartment in central Manchester

Premium Enjoyable 1-bedroom apartment in central Manchester
Manchester
The price is ￥16,320
￥32,897 total
includes taxes & fees
Oct 5 - Oct 6
Premium Enjoyable 1-bedroom apartment in central Manchester
A wooden deck with a railing, a door, and a view of trees.

14. 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
9.8 out of 10, Exceptional, (15 reviews)
"Nice private place to stay."
United States
Brian A.
The price is ￥20,446
￥26,659 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
A bedroom with a bed, a round table, a grey sofa, a window with a view of buildings, and a wooden wardrobe.

15. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
The price is ￥35,388
￥53,278 total
includes taxes & fees
Sep 28 - Sep 29
Trumbull Apartments
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

16. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (54 reviews)
"Very cute little place to spend a weekend! My friends, partner, and I slept comfortably. The lake itself is very nice (though weather unfortunately prevented us from going out on it with the kayaks) and it is within a short drive to Hartford, UConn, and plenty of things to do. Connecticut is such a lovely state! The purpose of our trip was so that my partner and I could look at apartments in town. We were already excited to move to CT, but after this trip, we became completely confident in how...
United States
Austin R.
The price is ￥21,209
￥47,727 total
includes taxes & fees
Sep 28 - Sep 29
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A hotel room with a bed, a nightstand, and a window with curtains.

17. 2-Bed Suite|Nsmk|Micfridge

2-Bed Suite|Nsmk|Micfridge
Enfield
8.8 out of 10, Excellent, (5 reviews)
The price is ￥14,939
￥17,181 total
includes taxes & fees
Sep 28 - Sep 29
2-Bed Suite|Nsmk|Micfridge
A lakeside view with a sandy beach, kayaks, and a 'No Dogs' sign.

18. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (49 reviews)
"Very peaceful and beautiful area. Well needed relaxing time. Highly recommend! Also Host was exceptional and attentive."
United States
Melissa
The price is ￥23,592
￥48,364 total
includes taxes & fees
Oct 19 - Oct 20
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A covered porch with wicker furniture, a potted plant, and a small table.

19. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (20 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 ￥19,209
￥58,711 total
includes taxes & fees
Oct 15 - Oct 16
The Blue Back Bungalow
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

20. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
The price is ￥22,019
￥46,555 total
includes taxes & fees
Oct 20 - Oct 21
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Quality Inn West Springfield

Quality Inn West Springfield

8/10 Good
"Average hotel, room was clean, good location"
Brittany 1-night trip
Posted 7 hours ago
Quality Inn West Springfield

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 9 vacation rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Historical Society and Oliver Ellsworth Homestead, whereas Northwest Park and Farmington River are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Loomis Chaffee School and Windsor Arts Center.

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.