A rustic barn surrounded by autumn foliage and a field.

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Our top choices for Windsor holiday rentals

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 £522
includes taxes & fees
16 Nov - 17 Nov
Windsor Retreat | Near Hartford & UConn College

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 £85
includes taxes & fees
20 Nov - 21 Nov
Entire guest suite in South Windsor, Connecticut

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 £67
includes taxes & fees
18 Nov - 19 Nov
1 Queen Bed | Micfridge

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 £67
includes taxes & fees
18 Nov - 19 Nov
1 Queen Bed | ADA/Tub/Micfridge

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 £144
includes taxes & fees
19 Nov - 20 Nov
Modern Private Furnished Studio Downtown Hartford

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.
The price is £160
includes taxes & fees
15 Nov - 16 Nov
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

7. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
The price is £59
includes taxes & fees
17 Nov - 18 Nov
1 King Bed|Smoking, Micfridge

8. 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 £213
includes taxes & fees
30 Nov - 1 Dec
The Serene Skyway Retreat

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.
The price is £159
includes taxes & fees
8 Dec - 9 Dec
Crested One Place - with Free Parking, Heat & AC

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
The price is £162
includes taxes & fees
15 Nov - 16 Nov
Central Chic Pad - with Free Parking, Heat & AC

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.
The price is £168
includes taxes & fees
19 Nov - 20 Nov
Fully Furnished Private Apartment, Elevator, Wi-Fi A/C

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 traveller
The price is £63
includes taxes & fees
17 Nov - 18 Nov
1 Queen Bed | Wethersfield

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 £166
includes taxes & fees
13 Dec - 14 Dec
Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay

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.
The price is £178
includes taxes & fees
15 Nov - 16 Nov
TruStay in Central CT

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 traveller
The price is £67
includes taxes & fees
22 Nov - 23 Nov
1 Queen Bed | Deluxe, Micfridge

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 £201
includes taxes & fees
15 Nov - 16 Nov
Lux Boutique Large Private LOFT Pratt St Hartford

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
The price is £126
includes taxes & fees
15 Nov - 16 Nov
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

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 £123
includes taxes & fees
20 Nov - 21 Nov
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

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.
The price is £225
includes taxes & fees
19 Nov - 20 Nov
The Blue Back Bungalow

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 traveller
The price is £63
includes taxes & fees
16 Nov - 17 Nov
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

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 £130 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 in Windsor close to Windsor Arts Center, 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?

Cabin Love at the Lake: This holiday home rental outside of Windsor offers a fireplace, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Windsor?

Expedia has 9 holiday 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 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.