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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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.
$611 nightly
The price is $696
Nov 17 - Nov 18
Total with taxes and fees
Windsor Retreat | Near Hartford & UConn College
A wooden deck with a table and two chairs, surrounded by a white railing.

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
$98 nightly
The price is $111
Nov 16 - Nov 17
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
A person in a blue shirt and black jacket walking towards a door with a red emergency button on the wall.

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 traveler
$77 nightly
The price is $88
Nov 17 - Nov 18
Total with taxes and fees
1 Queen Bed | Micfridge
A person in a blue shirt and black jacket walking towards a door with a red emergency button on the wall.

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 traveler
$77 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
1 Queen Bed | ADA/Tub/Micfridge
A modern kitchen with white cabinets, a black countertop, and a built-in stove.

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
$168 nightly
The price is $191
Nov 16 - Nov 17
Total with taxes and fees
Modern Private Furnished Studio Downtown Hartford
A multi-story building with a brick facade, large windows, and a street lamp.

6. 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.
$184 nightly
The price is $210
Nov 16 - Nov 17
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
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)
$67 nightly
The price is $77
Nov 16 - Nov 17
Total with taxes and fees
1 King Bed|Smoking, Micfridge
A kitchen with a wooden table, white cabinets, a built-in oven, and a window with a view.

8. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (19 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
$261 nightly
The price is $281
Nov 30 - Dec 1
Total with taxes and fees
The Serene Skyway Retreat
A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

9. 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.
$199 nightly
The price is $212
Nov 16 - Nov 17
Total with taxes and fees
Crested One Place - with Free Parking, Heat & AC
A living room with a dining area, a TV, and a large window with a view of buildings.

10. 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
$199 nightly
The price is $212
Nov 22 - Nov 23
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
A modern kitchen with a central island, stainless steel appliances, and black cabinets.

11. 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.
$195 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
Fully Furnished Private Apartment, Elevator, Wi-Fi A/C
A hotel reception area with a receptionist, a guest, and a child.

12. 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 traveler
$72 nightly
The price is $83
Nov 16 - Nov 17
Total with taxes and fees
1 Queen Bed | Wethersfield
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
$194 nightly
The price is $222
Nov 28 - Nov 29
Total with taxes and fees
Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay
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.

14. 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.
$219 nightly
The price is $234
Nov 16 - Nov 17
Total with taxes and fees
TruStay in Central CT
A person in a blue shirt and black jacket walking towards a door with a red emergency button on the wall.

15. 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 traveler
$77 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
1 Queen Bed | Deluxe, Micfridge
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.
$233 nightly
The price is $265
Nov 16 - Nov 17
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
A spacious bedroom with a large bed, a desk, and a seating area with chairs.

17. 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
$145 nightly
The price is $165
Nov 21 - Nov 22
Total with taxes and fees
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
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.
$142 nightly
The price is $162
Nov 16 - Nov 17
Total with taxes and fees
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
A two-story white house with a red door, surrounded by lush greenery and a paved driveway.

19. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (22 reviews)
"Nice two story home on a quiet street. Clesn and well supplied. Homey decor and decorative touches. Nice front porch to sit in and drink our coffee. We enjoyed staying there."
United States
James K.
$282 nightly
The price is $299
Dec 2 - Dec 3
Total with taxes and fees
The Blue Back Bungalow
A hotel reception area with a receptionist, a guest, and a child.

20. 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 traveler
$72 nightly
The price is $83
Nov 16 - Nov 17
Total with taxes and fees
1 Queen Bed | Smoking
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

Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

8/10 Good
"Layout interesting and access to back door was helpful as I ws able to get in easily"
Sandra 2-night trip
Posted 8 hours ago
Courtyard By Marriott Hartford/Windsor Airport

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.