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

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (21)
"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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
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
Bring Your Pet & Visit Springfield: Westfield Home
Outdoor dining

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.4 out of 10, (10)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

The price is HK$1,075
HK$2,571 total
includes taxes & fees
21 Jul - 22 Jul
Charming Chicopee Getaway
Mountaintop Horse Farm with Heated Pool
Outdoor pool, a heated pool

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (29)
"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "
Mountaintop Horse Farm with Heated Pool
Cozy apartment in charming Hartford with AC, WiFi
Private kitchen

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (1)
The price is HK$903
HK$1,331 total
includes taxes & fees
20 Jul - 21 Jul
Cozy apartment in charming Hartford with AC, WiFi
Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

9.0 out of 10, Wonderful, (17)
"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."
The price is HK$1,091
HK$1,547 total
includes taxes & fees
1 Aug - 2 Aug
Lux Boutique Large Private LOFT Pratt St Hartford
HOMEY HOMEY

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is HK$565
HK$1,309 total
includes taxes & fees
12 Jul - 13 Jul
HOMEY HOMEY
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!
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is HK$1,570
HK$2,821 total
includes taxes & fees
27 Jul - 28 Jul
Big farmhouse in the foothills of the Berkshires
5 bedroom in the center of Springfield .
Interior

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (7)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Fridge, microwave, oven, coffee/tea maker

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

7.6 out of 10, Good, (7)
"Overall, this property is honestly one of the nicest homes I’ve stayed at. The kitchen was nice and big and the bathroom was so pretty. I enjoyed my stay it was very nice and would love to come and stay again. I recommend this home !! The neighbor is also very nice ! they helped me find my parking spot! ❤️"
The price is HK$1,044
HK$2,559 total
includes taxes & fees
12 Jul - 13 Jul
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Property grounds

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (7)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Microwave, electric kettle, cookware/dishes/utensils, paper towels

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

10.0 out of 10, Exceptional, (1)
"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."
The price is HK$824
HK$1,572 total
includes taxes & fees
13 Jul - 14 Jul
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Fridge, microwave, oven, stovetop

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Spa

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

2.0 star property
10.0 out of 10, Exceptional, (12)
"What a lovely studio!! Checking in and out was so easy. The studio looks just like the pictures. The hosts had everything there that one would need except an iron/board. Quaint little town with limited dining choices but many options near by. We will definitely use this place again."
The price is HK$812
HK$1,362 total
includes taxes & fees
13 Jul - 14 Jul
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.4 out of 10, Exceptional, (13)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is HK$801
HK$2,789 total
includes taxes & fees
22 Jul - 23 Jul
Blue Back Bungalow
Charming Farmhouse w/ Pool & Fishing Pond!
Fridge, microwave, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (13)
"Everything about the house and property was exactly as described. We had the best time there with plenty of space to spread out. It was very clean and comfortable. The kids had so much fun exploring and they visited the ice cream shop everyday that it was open.We will definitely stay here again."
Charming Farmhouse w/ Pool & Fishing Pond!
Modern Condo|DWNTN Hartord| XL Center| GYM
Fridge, microwave, oven, stovetop

Modern Condo|DWNTN Hartord| XL Center| GYM

4.0 out of 10, (1)
"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."
The price is HK$801
HK$1,593 total
includes taxes & fees
15 Jul - 16 Jul
Modern Condo|DWNTN Hartord| XL Center| GYM
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.