Old tobacco barn with oak trees

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Windsor holiday rentals

Fridge, microwave, oven, stovetop

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
9.8 out of 10, Exceptional, (7 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is HK$2,045
HK$4,217 total
includes taxes & fees
23 Jun - 24 Jun
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Property grounds

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (50 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is HK$1,600
HK$3,024 total
includes taxes & fees
6 Jul - 7 Jul
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is HK$1,489
HK$2,783 total
includes taxes & fees
2 Jul - 3 Jul
Big farmhouse in the foothills of the Berkshires
Living area

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is HK$3,663
HK$5,331 total
includes taxes & fees
23 Jun - 24 Jun
Newly Renovated 2 floor Getaway
Smart TV

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

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (23 reviews)
"Was a great stay"
United States
John S.
The price is HK$1,168
HK$2,463 total
includes taxes & fees
29 Jun - 30 Jun
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$940
HK$1,238 total
includes taxes & fees
21 Jun - 22 Jun
Humble Abode #2
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
2BR Apartment Near Wesleyan 301
Smart TV, books

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
10.0 out of 10, Exceptional, (4 reviews)
"Perfect place to stay when using it as a base camp to get around the are. Excellent communication from the host. She made it easy to stay there."
United States
Aaron C.
The price is HK$987
HK$2,181 total
includes taxes & fees
21 Jun - 22 Jun
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Interior

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is HK$611
HK$2,144 total
includes taxes & fees
21 Jun - 22 Jun
The Historic Hideaway
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is HK$1,128
HK$2,434 total
includes taxes & fees
22 Jun - 23 Jun
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (44 reviews)
"We had an awesome stay for Thanksgiving week!"
United States
Jamie S.
The price is HK$1,414
HK$2,810 total
includes taxes & fees
30 Jun - 1 Jul
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, (4 reviews)
"I had a great one night stay. Place was super clean and fresh. If I’m ever in the area I’ll stay there again for sure. It was a pleasure."
United States
debo9412
The price is HK$752
HK$1,022 total
includes taxes & fees
7 Jul - 8 Jul
Entire guest suite in South Windsor, Connecticut
Combined shower/bathtub, hair dryer, towels, soap

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.0 out of 10, Wonderful, (30 reviews)
"Great. Placeto stay"
United States
Anonymous traveller
The price is HK$2,468
HK$4,356 total
includes taxes & fees
21 Jun - 22 Jun
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Interior

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (40 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$1,213
HK$2,508 total
includes taxes & fees
24 Jun - 25 Jun
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is HK$1,191
HK$2,231 total
includes taxes & fees
21 Jun - 22 Jun
#26 Beautifully Renovated 2 BR Home
Smart TV, offices, computer monitors

TruStay in Central CT

TruStay in Central CT
Manchester
The price is HK$820
HK$1,844 total
includes taxes & fees
21 Jun - 22 Jun
TruStay in Central CT
3 bedrooms, free WiFi

Location, is the key for this 3 bedroom!

Location, is the key for this 3 bedroom!
Frog Hollow
9.2 out of 10, Wonderful, (5 reviews)
"It was nice and close to where we had a wedding. Plenty of room for us all. Host was very easy to contact. "
United States
Shawn R.
The price is HK$1,382
HK$3,498 total
includes taxes & fees
22 Jun - 23 Jun
Location, is the key for this 3 bedroom!
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$1,234
HK$1,944 total
includes taxes & fees
2 Jul - 3 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Shower, towels, shampoo

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
3 BR Apartment Near Wesleyan 202
Fridge, microwave, oven, stovetop

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is HK$2,171
HK$4,315 total
includes taxes & fees
24 Jun - 25 Jun
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
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

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"Love this Best Western, they are the best, always go beyond what you would expect"
Lovett 1-night trip
Posted 2 hours ago
Best Western Hartford Hotel & Suites

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?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This highly rated holiday home rental in Windsor has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 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 Windsor Arts Center and Loomis Chaffee School.

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.