Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor vacation rentals

A garden pathway leading to a white arbor with pink flowers, surrounded by lush greenery and a clear sky.

1. Windsor Retreat | Near Hartford & UConn College

Windsor Retreat | Near Hartford & UConn College
Windsor
9.4 out of 10, Exceptional, (13 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 CA $398
CA $983 total
includes taxes & fees
Nov 23 - Nov 24
Windsor Retreat | Near Hartford & UConn College
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
10.0 out of 10, Exceptional, (13 reviews)
"Good location"
United States
Arthur
The price is CA $121
CA $156 total
includes taxes & fees
Nov 16 - Nov 17
Entire guest suite in South Windsor, Connecticut
A reception area with a counter, a plant, and an exit sign.

3. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (51 reviews)
"Near the airport, this place made for a quick and easy stay."
United States
Anonymous traveller
The price is CA $110
CA $126 total
includes taxes & fees
Nov 9 - Nov 10
1 Queen Bed | Micfridge
A reception area with a counter, a plant, and an exit sign.

4. 1 Queen Bed | ADA/Tub/Micfridge

1 Queen Bed | ADA/Tub/Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (53 reviews)
"The pool area was clean and relaxing, perfect for unwinding after a busy day."
United States
Anonymous traveller
The price is CA $110
CA $126 total
includes taxes & fees
Nov 9 - Nov 10
1 Queen Bed | ADA/Tub/Micfridge
A modern bedroom with a large bed, a wooden wardrobe, a small round table, and a window with blinds.

5. Modern Private Furnished Studio Downtown Hartford

Modern Private Furnished Studio Downtown Hartford
Downtown Hartford
7.4 out of 10, Good, (3 reviews)
"I had wondered about the amenities. the coffee pot was not cleaned , actually had mold in it , and the carpet was lifting at one corner, where i kept tripping on it. I certainly appreciated the rest ! As it was during the turkey holiday and easy to find through downtown Hartford "
United States
Lynnett
The price is CA $126
CA $267 total
includes taxes & fees
Nov 9 - Nov 10
Modern Private Furnished Studio Downtown Hartford
A living room with a dining area, a TV, and a large window with a view of buildings.

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

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.4 out of 10, Exceptional, (8 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is CA $121
CA $286 total
includes taxes & fees
Nov 9 - Nov 10
Central Chic Pad - with Free Parking, Heat & AC
A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

7. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $96
CA $110 total
includes taxes & fees
Nov 9 - Nov 10
1 King Bed|Smoking, Micfridge
A multi-story building with a brick facade, large windows, and a street lamp.

8. Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Nice place"
United States
Bonita T.
The price is CA $147
CA $292 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

9. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (18 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is CA $124
CA $390 total
includes taxes & fees
Nov 30 - Dec 1
The Serene Skyway Retreat
A modern living room with a gray sofa, a coffee table, and a dining area with a table and chairs. There is a TV and a plant in the room.

10. 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 CA $147
CA $317 total
includes taxes & fees
Nov 9 - Nov 10
TruStay in Central CT
A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

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

Crested One Place - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place for a quick stay"
United States
phillip s.
The price is CA $121
CA $295 total
includes taxes & fees
Nov 11 - Nov 12
Crested One Place - with Free Parking, Heat & AC
A modern kitchen with a central island, stainless steel appliances, and black cabinets.

12. Fully Furnished Private Apartment, Elevator, Wi-Fi A/C

Fully Furnished Private Apartment, Elevator, Wi-Fi A/C
Downtown Hartford
9.0 out of 10, Wonderful, (2 reviews)
"Great place downtown Hartford! Clean and quiet and minutes from everything! My only issue was that it claims to be fully furnished but there is no iron or steamer. Guests are often traveling in for events so having that on hand is essential. Other than that all was wonderful!"
United States
Shea O.
The price is CA $147
CA $301 total
includes taxes & fees
Nov 9 - Nov 10
Fully Furnished Private Apartment, Elevator, Wi-Fi A/C
A kitchen cabinet with shelves holding glasses, bowls, and plates.

13. Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay

Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay
Manchester
The price is CA $141
CA $301 total
includes taxes & fees
Nov 9 - Nov 10
Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay
A kitchen with wooden shelves, a toaster, and a sink.

14. 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, (29 reviews)
"The interior is exactly as the photos showed. Kudos to the interior design. The unit itself is on the 1st floor of a 2 story building, situated next to the street. The traffic slows down at night so one doesn't get bothered by the noise. We have a parking area right in front of the unit. We can hear the upstairs traffic but it's not constant. The bathroom is very small. The unit has low ceiling so it may not be suited for very tall people. It is a compact unit, but it has very thing we...
United States
Tom
The price is CA $187
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
A hotel reception area with a receptionist, a guest, and a child.

15. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Quick check-in and quiet room helped us get good rest before hitting the road again."
United States
Anonymous traveller
The price is CA $103
CA $118 total
includes taxes & fees
Nov 11 - Nov 12
1 Queen Bed | Wethersfield
A modern kitchen with black cabinets, a white countertop, and a built-in oven.

16. Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.4 out of 10, Very good, (30 reviews)
"Great stay"
United States
Josh H.
The price is CA $189
CA $363 total
includes taxes & fees
Nov 9 - Nov 10
Lux Boutique Large Private LOFT Pratt St Hartford
A reception area with a counter, a plant, and an exit sign.

17. 1 Queen Bed | Deluxe, Micfridge

1 Queen Bed | Deluxe, Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (53 reviews)
"Good location near the airport, clean rooms, straightforward setup for travelers."
United States
Anonymous traveller
The price is CA $110
CA $126 total
includes taxes & fees
Nov 9 - Nov 10
1 Queen Bed | Deluxe, Micfridge
A wooden deck with a railing, a door, and a view of trees.

18. 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
9.6 out of 10, Exceptional, (18 reviews)
"Nice private place to stay."
United States
Brian A.
The price is CA $182
CA $217 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
A hotel reception area with a receptionist, a guest, and a child.

19. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple rooms close to I-91 made travel convenient."
United States
Anonymous traveller
The price is CA $103
CA $118 total
includes taxes & fees
Nov 9 - Nov 10
1 Queen Bed | Smoking
A modern kitchen with black cabinets, a white countertop, and a built-in oven.

20. Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC
Downtown Hartford
8.6 out of 10, Excellent, (14 reviews)
"Great location, very nice and clean. "
United States
Manuel M.
The price is CA $189
CA $358 total
includes taxes & fees
Nov 11 - Nov 12
Totally Private Cozy studio in awesome Hartford with WiFi, AC
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

An outdoor dining area with tables and chairs, surrounded by plants and trees.
Delamar West Hartford

Delamar West Hartford

Delamar West Hartford
West Hartford

10/10 Excellent

Second time staying at the Delmar and it was fantastic.
Canada
Sarah
Reviewed August 26, 2026
Delamar West Hartford

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $264 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Cabin Love at the Lake: This vacation home rental outside of Windsor offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.