Windsor Holiday Rentals

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Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Windsor

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

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

9.8 out of 10, Exceptional, (23)
"This property had easy access to the lake and had nice character. it was a quick overnight and wished we had more time to enjoy it. Kitchen pots and pans and bath towels could be updated. Bathroom door needs attention as its hard to close."
The price is HK$1,782
HK$3,273 total
includes taxes & fees
21 Jul - 22 Jul
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Cozy basement apartment with private bathroom, kitchen and entrance.
Smart TV

Cozy basement apartment with private bathroom, kitchen and entrance.

The price is HK$1,236
HK$3,832 total
includes taxes & fees
14 Jul - 15 Jul
Cozy basement apartment with private bathroom, kitchen and entrance.
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Fridge, microwave, oven, stovetop

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

10.0 out of 10, Exceptional, (1)
"Spacious, clean and comfortable home. Nice neighborhood near a nice park and trails . Beds were comfortable, kitchen had the pots and pans we needed for dinner and breakfast. Perfect space for us and our 3 adult boys. "
The price is HK$1,248
HK$2,597 total
includes taxes & fees
15 Jul - 16 Jul
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Modern & Cozy Cape | 4 Bedroom House | Central Location
Fridge, microwave, oven, stovetop

Modern & Cozy Cape | 4 Bedroom House | Central Location

10.0 out of 10, Exceptional, (5)
"We had a great stay in this house. It provided everything we needed for a comfortable and enjoyable visit. All the rooms were clean, tidy, and well-maintained, creating a welcoming environment. The host was exceptionally helpful and quick to respond to any questions or needs we had, which made our experience even better. We highly recommend this house for anyone looking for a hassle-free and pleasant stay."
The price is HK$1,020
HK$2,312 total
includes taxes & fees
16 Jul - 17 Jul
Modern & Cozy Cape | 4 Bedroom House | Central Location
15mins to Hartford, Home in Manchester w/ King Bed
Fridge, microwave, oven, stovetop

15mins to Hartford, Home in Manchester w/ King Bed

2.0 star property
8.6 out of 10, Excellent, (4)
"This property is a great place to stay, it was clean and well looked after. The owner kept in contact throughout our stay. Definitely recommend this property Thankyou"
The price is HK$1,055
HK$2,383 total
includes taxes & fees
17 Jul - 18 Jul
15mins to Hartford, Home in Manchester w/ King Bed
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (10)
"House was great & close to where we needed to be. "
The price is HK$1,154
HK$2,481 total
includes taxes & fees
15 Jul - 16 Jul
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Modern Luxury, The Perfect Getaway Awaits
Fridge, oven, stovetop, dishwasher

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (1)
The price is HK$2,292
HK$4,159 total
includes taxes & fees
13 Jul - 14 Jul
Modern Luxury, The Perfect Getaway Awaits
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Private kitchen

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

9.0 out of 10, Wonderful, (2)
"Mini family vacation. The property was pleasant and convenient to the Museums and Zoo.This is not specific to this stay, but I wish the fees would be available prior to the booking/ payment process. We had to stop the booking of a different property for this trip when the hidden fees more than doubled the cost of the rental."
The price is HK$1,625
HK$2,850 total
includes taxes & fees
17 Jul - 18 Jul
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

9.0 out of 10, Wonderful, (9)
"My family of five was pleasantly pleased with our booking. The duplex had plenty of space, including access to the basement. Easy access, adequate parking, safe neighborhood, clean surfaces and extra linen, around plenty of food options and great wi-fi connection. All instructions were simple and easy to follow. It snowed during our stay and we woke up to the porch and sidewalk shoveled! Chef's Kiss A"
The price is HK$1,099
HK$2,681 total
includes taxes & fees
16 Jul - 17 Jul
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Dining

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

9.2 out of 10, Wonderful, (9)
"Great stay"
The price is HK$1,099
HK$2,690 total
includes taxes & fees
3 Aug - 4 Aug
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (9)
"Our experience with this facility, from online service to exiting the residence, was the most pleasurable experience, for staying in accommodations when traveling!!The owner was a complete gentleman and it was absolutely wonderful experience to meet and talk with him."
The price is HK$1,798
HK$2,825 total
includes taxes & fees
11 Aug - 12 Aug
Family Stays: Middletown, CT
PICON COZY
Fridge, microwave, oven, stovetop

PICON COZY

7.6 out of 10, Good, (67)
"Peaceful "
The price is HK$530
HK$1,269 total
includes taxes & fees
13 Jul - 14 Jul
PICON COZY
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (31)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is HK$1,531
HK$2,583 total
includes taxes & fees
31 Jul - 1 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Newly Beautiful renovated first floor apartment getaway
Fridge, microwave, oven, stovetop

Newly Beautiful renovated first floor apartment getaway

8.0 out of 10, Very good, (1)
"We had an amazing time. This property was easy to find and very close to aloy of restaurants and shops! We had amazing chinese food! The apartment felt very homey. I love that it wasnt echo-y like past places I have stayed! I met Rose, the host, and she was super nice. She was very responsive and explained everything I needed to know before I arrived at the property. Also she lives near by and can address any problems or concerns you may have. The photography on the walls were gorgeous, the...
The price is HK$1,413
HK$2,770 total
includes taxes & fees
23 Jul - 24 Jul
Newly Beautiful renovated first floor apartment getaway
Beautiful 4BR 2 Bathroom House with Parking
Fridge, microwave, oven, stovetop

Beautiful 4BR 2 Bathroom House with Parking

9.8 out of 10, Exceptional, (9)
"Very clean, pleasant, and comfortable. We pretty much just slept there as we were at familie's houses during the day, but it was a wonderful place for us to sleep at night."
The price is HK$2,669
HK$5,486 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful 4BR 2 Bathroom House with Parking
Stylish 4BR 2 Bathroom Home in Forest Park
Fridge, microwave, oven, stovetop

Stylish 4BR 2 Bathroom Home in Forest Park

10.0 out of 10, Exceptional, (2)
"The house was in a great location it was minutes away from the Big E Fairgrounds and MGM Casino."
The price is HK$2,590
HK$5,397 total
includes taxes & fees
15 Jul - 16 Jul
Stylish 4BR 2 Bathroom Home in Forest Park
Charming 3 bed/2 bath town home with gorgeous back yard
Property grounds

Charming 3 bed/2 bath town home with gorgeous back yard

9.8 out of 10, Exceptional, (12)
"Beautifully updated unit with all the amenities of home. Very quiet, safe neighborhood with nearby stores and restaurants. Great value for a short stay…"
The price is HK$3,850
HK$4,992 total
includes taxes & fees
16 Jul - 17 Jul
Charming 3 bed/2 bath town home with gorgeous back yard
Modern Victorian 3BR 2BA Apt with Parking
3 bedrooms, bed sheets

Modern Victorian 3BR 2BA Apt with Parking

The price is HK$2,716
HK$5,201 total
includes taxes & fees
14 Jul - 15 Jul
Modern Victorian 3BR 2BA Apt with Parking
Elegant 7Bed 2.5Bath Victorian Home
Private kitchen

Elegant 7Bed 2.5Bath Victorian Home

"Apt was very spacious and welcoming. Kitchen gets really warm when you cook but with ac units in every room the rest of the house is comfortable. Definitely a place to stay. "
The price is HK$5,887
HK$9,867 total
includes taxes & fees
14 Jul - 15 Jul
Elegant 7Bed 2.5Bath Victorian Home
Saint James Manor - Sleeps 20+ in Style & Comfort with Parking
11 bedrooms, iron/ironing board, WiFi, bed sheets

Saint James Manor - Sleeps 20+ in Style & Comfort with Parking

The price is HK$9,420
HK$15,896 total
includes taxes & fees
14 Jul - 15 Jul
Saint James Manor - Sleeps 20+ in Style & Comfort with Parking
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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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?

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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 Historical Society.

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.