Windsor Vacation Rentals

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Vacation Rentals in Windsor

Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

8.8 out of 10, Excellent, (48)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
$230 nightly
The price is $262
Dec 10 - Dec 11
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Vacation Home in Coventry Lake

9.8 out of 10, Exceptional, (34)
"Comfortable and as described "
United States
Stephanie
$247 nightly
The price is $280
Dec 4 - Dec 5
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Exterior
The Blue Back Bungalow

Apartment in West Hartford

2.0 star property
9.4 out of 10, Exceptional, (17)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
$293 nightly
The price is $310
Dec 7 - Dec 8
Total with taxes and fees
The Blue Back Bungalow
Fridge, microwave, oven, stovetop
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!

Apartment in Manchester

10.0 out of 10, Exceptional, (2)
"Very nice apartment space, fully equipped."
United States
Michele M.
$272 nightly
The price is $308
Dec 4 - Dec 5
Total with taxes and fees
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

9.6 out of 10, Exceptional, (38)
"Pet and family, friendly"
United States
Mary-Kate G
$269 nightly
The price is $305
Dec 10 - Dec 11
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds
Humble Abode #2

Apartment in Manchester Center

2.0 star property
$116 nightly
The price is $130
Dec 4 - Dec 5
Total with taxes and fees
Humble Abode #2
Dining
The Serene Skyway Retreat

Vacation Home in Windsor Locks

8.8 out of 10, Excellent, (11)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
$256 nightly
The price is $272
Dec 6 - Dec 7
Total with taxes and fees
The Serene Skyway Retreat
Outdoor dining
The Historic Hideaway

Apartment in Avon

2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
$231 nightly
The price is $243
Dec 5 - Dec 6
Total with taxes and fees
The Historic Hideaway
Dining
#24 *Serenity* A Lakefront Cottage Retreat

Vacation Home in Middletown

9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
$275 nightly
The price is $293
Dec 10 - Dec 11
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
$246 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Terrace/patio
Peaceful Meadow Retreat

Apartment in Granby

2.0 star property
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
$176 nightly
The price is $200
Dec 7 - Dec 8
Total with taxes and fees
Peaceful Meadow Retreat
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Vacation Home in Boston Road

9.2 out of 10, Wonderful, (13)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
$283 nightly
The price is $321
Dec 7 - Dec 8
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Dining
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Vacation Home in Boston Road

9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
$283 nightly
The price is $321
Dec 4 - Dec 5
Total with taxes and fees
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Apartment in Downtown Hartford

9.6 out of 10, Exceptional, (5)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
United States
Hoyt
$170 nightly
The price is $193
Dec 4 - Dec 5
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Property grounds
One private bedroom with work space and shared home with spa.

Vacation Home in Rocky Hill

$122 nightly
The price is $137
Dec 4 - Dec 5
Total with taxes and fees
One private bedroom with work space and shared home with spa.
Fridge, microwave, oven, stovetop
Modern & Cozy Cape | 4 Bedroom House | Central Location

Vacation Home in Manchester Center

10.0 out of 10, Exceptional, (5)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
$258 nightly
The price is $292
Dec 7 - Dec 8
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
TV
Modern Living: 1-BR Near XLCenter|ConventionCenter

Apartment in Downtown Hartford

$216 nightly
The price is $216
Dec 7 - Dec 8
Total with taxes and fees
Modern Living: 1-BR Near XLCenter|ConventionCenter
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

Vacation Home in Plainville

10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
$196 nightly
The price is $210
Dec 10 - Dec 11
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
Smart TV
Premier League Pad - with Free Parking, Heat & AC

Apartment in Manchester

10.0 out of 10, Exceptional, (3)
"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.
$227 nightly
The price is $244
Dec 9 - Dec 10
Total with taxes and fees
Premier League Pad - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop
Family Stays: Middletown, CT

Vacation Home in Middletown

10.0 out of 10, Exceptional, (18)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
$203 nightly
The price is $230
Dec 15 - Dec 16
Total with taxes and fees
Family Stays: Middletown, CT
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"The room was immaculate. Very cozy and comfortable. The mattress was ok but I’m picky about what I sleep on. It could’ve been a little more structured, it seemed kind of old and uneven. "
Sandra 1-night trip
Posted 1 day ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

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 $152 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 close to popular points of interest in Windsor, or you can select a more secluded option if you're looking for relaxation. 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?

A “Wow” Experience everywhere there is something to stimulate your mind Interest: This highly rated vacation home rental in Windsor offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 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 garden.

How many vacation rentals are there in Windsor?

Expedia has 6 vacation rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Arts Center and Vintage Radio and Communications Museum of Connecticut, 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 Oliver Ellsworth Homestead.

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.