Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

8.8 out of 10, Excellent, (48)
"It was great! Thank you :-) "
United States
Becki S.
The price is AU$427
includes taxes & fees
4 Jan - 5 Jan
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.8 out of 10, Exceptional, (35)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is AU$488
includes taxes & fees
4 Jan - 5 Jan
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is AU$240
includes taxes & fees
3 Jan - 4 Jan
Humble Abode #2

Condo in Pine Point

Welcome to Honey Spot!
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is AU$446
includes taxes & fees
5 Jan - 6 Jan
Welcome to Honey Spot!
10.0 out of 10, Exceptional, (6)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is AU$300
includes taxes & fees
6 Jan - 7 Jan
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is AU$325
includes taxes & fees
3 Jan - 4 Jan
Cozy Guest Suite in Historic Home
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is AU$490
includes taxes & fees
12 Jan - 13 Jan
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Apartment in Avon

The Historic Hideaway
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.
The price is AU$371
includes taxes & fees
9 Jan - 10 Jan
The Historic Hideaway
10.0 out of 10, Exceptional, (2)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
9.2 out of 10, Wonderful, (13)
"For the most part everything was great!"
United States
Gabriel M.
The price is AU$486
includes taxes & fees
3 Jan - 4 Jan
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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 AU$291
includes taxes & fees
4 Jan - 5 Jan
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
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 AU$367
includes taxes & fees
1 Feb - 2 Feb
Premier League Pad - with Free Parking, Heat & AC
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is AU$318
includes taxes & fees
13 Jan - 14 Jan
Central Chic Pad - with Free Parking, Heat & AC

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is AU$456
includes taxes & fees
4 Jan - 5 Jan
Private Apartment in Berlin

Holiday Home in Plainville

#26 Beautifully Renovated 2 BR Home
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.
The price is AU$358
includes taxes & fees
24 Jan - 25 Jan
#26 Beautifully Renovated 2 BR Home

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (17)
"Beautiful property comfy, cozy and clean little cottage."
United States
Denise T.
The price is AU$280
includes taxes & fees
6 Jan - 7 Jan
Peaceful Meadow Retreat
9.4 out of 10, Exceptional, (15)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is AU$404
includes taxes & fees
5 Jan - 6 Jan
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
2.0 star property
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is AU$510
includes taxes & fees
5 Jan - 6 Jan
Welcoming 3-bedroom house- Gardner home

Apartment in Chicopee

Charming Chicopee Getaway
7.6 out of 10, Good, (4)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
Charming Chicopee Getaway
The price is AU$320
includes taxes & fees
4 Jan - 5 Jan
Crested One Place - with Free Parking, Heat & 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

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, 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 favourite 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 depend 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 AU$231 per night. Entering your travel dates in the search wizard might find you 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 7 holiday rentals for your stay in Windsor.

What can I see and do in Windsor?

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

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.