Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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.
The price is €228
includes taxes & fees
4 Dec - 5 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

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.
The price is €274
includes taxes & fees
2 Dec - 3 Dec
The Blue Back Bungalow

Apartment in Manchester

10.0 out of 10, Exceptional, (2)
"Very nice apartment space, fully equipped."
United States
Michele M.
The price is €274
includes taxes & fees
1 Dec - 2 Dec
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!

Holiday 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.
The price is €259
includes taxes & fees
5 Dec - 6 Dec
#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home in Coventry Lake

9.8 out of 10, Exceptional, (34)
"Comfortable and as described "
United States
Stephanie
The price is €247
includes taxes & fees
30 Nov - 1 Dec
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

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.
The price is €246
includes taxes & fees
1 Dec - 2 Dec
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Manchester Center

2.0 star property
The price is €116
includes taxes & fees
26 Dec - 27 Dec
Humble Abode #2

Cabin in Coventry Lake

9.6 out of 10, Exceptional, (38)
"Pet and family, friendly"
United States
Mary-Kate G
The price is €267
includes taxes & fees
16 Dec - 17 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

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
The price is €176
includes taxes & fees
1 Dec - 2 Dec
Peaceful Meadow Retreat

Holiday Home in New Britain

9.0 out of 10, Wonderful, (2)
"This stay was very comfortable and also not too fat from the Convention Center either "
United States
Vicente B.
The price is €192
includes taxes & fees
30 Nov - 1 Dec
#28- *Modern Bungalow*

Holiday 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.
The price is €258
includes taxes & fees
30 Nov - 1 Dec
Modern & Cozy Cape | 4 Bedroom House | Central Location

Apartment in Downtown Hartford

The price is €178
includes taxes & fees
2 Dec - 3 Dec
Modern Living: 1-BR Near XLCenter|ConventionCenter

Apartment in West Hartford

2.0 star property
The price is €179
includes taxes & fees
3 Dec - 4 Dec
Nearest to Blue Back Square - Affordable w/ KING Bed

Apartment in Downtown Hartford

7.0 out of 10, Good, (4)
"The photos made the property look better than it was. The space wasn’t as clean as I’d expect and it was not very well appointed. There were no hand towels, the microwave didn’t work, there was no ice or way to make ice. It just wasn’t what I expected. "
United States
Heather C.
The price is €196
includes taxes & fees
1 Dec - 2 Dec
Hartford Cityscape|Bushnell Park|Downtown Skyline

Holiday 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.
The price is €241
includes taxes & fees
6 Dec - 7 Dec
The Serene Skyway Retreat

Holiday 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.
Family Stays: Middletown, CT

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.
The price is €216
includes taxes & fees
7 Dec - 8 Dec
Premier League Pad - with Free Parking, Heat & AC

Holiday 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.
#26 Beautifully Renovated 2 BR Home

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
The price is €172
includes taxes & fees
16 Dec - 17 Dec
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Holiday Home in Rocky Hill

The price is €122
includes taxes & fees
1 Dec - 2 Dec
One private bedroom with work space and shared home with spa.
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €135 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 holiday 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 holiday.

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 holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What are some of the best holiday rentals that Windsor has to offer?

A “Wow” Experience everywhere there is something to stimulate your mind Interest: This highly rated holiday home rental in Windsor offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Windsor?

Expedia has 6 holiday 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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.