Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Windsor holiday rentals

Interior

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (36 reviews)
"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 HK$1,076
HK$2,292 total
includes taxes & fees
8 Mar - 9 Mar
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$937
HK$1,233 total
includes taxes & fees
6 Mar - 7 Mar
Humble Abode #2
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5 reviews)
"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 HK$944
HK$2,202 total
includes taxes & fees
8 Mar - 9 Mar
Modern & Cozy Cape | 4 Bedroom House | Central Location
Fridge, microwave, stovetop, coffee/tea maker

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
10.0 out of 10, Exceptional, (22 reviews)
"Clean place, simple check in, over great!"
United States
Allison S.
The price is HK$1,040
HK$1,352 total
includes taxes & fees
8 Mar - 9 Mar
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Smart TV

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is HK$673
HK$1,617 total
includes taxes & fees
16 Mar - 17 Mar
Crested One Place - with Free Parking, Heat & AC
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is HK$1,161
HK$2,670 total
includes taxes & fees
9 Mar - 10 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
The price is HK$767
HK$2,180 total
includes taxes & fees
19 Mar - 20 Mar
2BR Apartment Near Wesleyan 301
Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.2 out of 10, Wonderful, (40 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is HK$1,352
HK$2,728 total
includes taxes & fees
1 Apr - 2 Apr
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is HK$674
HK$932 total
includes taxes & fees
12 Mar - 13 Mar
Entire guest suite in South Windsor, Connecticut
Microwave, oven, stovetop, dishwasher

One private bedroom with work space and shared home with spa.

One private bedroom with work space and shared home with spa.
Rocky Hill
The price is HK$808
HK$1,175 total
includes taxes & fees
6 Mar - 7 Mar
One private bedroom with work space and shared home with spa.
Exterior

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
9.4 out of 10, Exceptional, (6 reviews)
"Great location. Clean property"
United States
Sue R.
The price is HK$898
HK$1,772 total
includes taxes & fees
8 Mar - 9 Mar
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

XL Center Downtown Condo w/ Onsite Parking and Gym

XL Center Downtown Condo w/ Onsite Parking and Gym
Downtown Hartford
7.4 out of 10, Good, (3 reviews)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveller
The price is HK$935
HK$2,112 total
includes taxes & fees
8 Mar - 9 Mar
XL Center Downtown Condo w/ Onsite Parking and Gym
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12 reviews)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is HK$710
HK$2,236 total
includes taxes & fees
17 Mar - 18 Mar
The Serene Skyway Retreat

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is HK$749
HK$2,134 total
includes taxes & fees
9 Mar - 10 Mar
2BR Apartment Near Wesleyan 102
Interior

Fully Furnished Private Studio . Free GYM, Free Utilities, Free Parking & Wifi

Fully Furnished Private Studio . Free GYM, Free Utilities, Free Parking & Wifi
Downtown Hartford
The price is HK$878
HK$1,788 total
includes taxes & fees
6 Mar - 7 Mar
Fully Furnished Private Studio . Free GYM, Free Utilities, Free Parking & Wifi
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (22 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$898
HK$1,758 total
includes taxes & fees
16 Mar - 17 Mar
Family Stays: Middletown, CT
Interior

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (7 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is HK$937
HK$1,547 total
includes taxes & fees
15 Mar - 16 Mar
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.6 out of 10, Exceptional, (19 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$929
HK$2,184 total
includes taxes & fees
9 Mar - 10 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
WiFi, bed sheets

Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC
Downtown Hartford
8.6 out of 10, Excellent, (11 reviews)
"Great location, very nice and clean. "
United States
Manuel M.
The price is HK$780
HK$1,637 total
includes taxes & fees
10 Mar - 11 Mar
Totally Private Cozy studio in awesome Hartford with WiFi, AC
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is HK$808
HK$3,022 total
includes taxes & fees
8 Mar - 9 Mar
Willow Haven 2BR Cozy Retreat, Close to Hartford
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Very clean, good food "
Richet 1-night trip
Posted 3 days ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Big farmhouse in the foothills of the Berkshires: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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 Oliver Ellsworth Homestead 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 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.