Windsor Holiday Rentals

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Holiday Rentals in Windsor

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

9.4 out of 10, Exceptional, (21)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Island Vibes Home

9.4 out of 10, Exceptional, (18)
"Our stay was great! We enjoyed the clean and spacious bedrooms! Super easy and everything was as listed. "
Island Vibes Home

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 AU$658
includes taxes & fees
6 Aug - 7 Aug
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Charming Chicopee Getaway

The price is AU$519
includes taxes & fees
2 Aug - 3 Aug
Charming Chicopee Getaway

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 AU$302
includes taxes & fees
9 Aug - 10 Aug
Lux Boutique Large Private LOFT Pratt St Hartford

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is AU$244
includes taxes & fees
28 July - 29 July
PICON COZY

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (1)
The price is AU$260
includes taxes & fees
29 July - 30 July
Cozy apartment in charming Hartford with AC, WiFi

Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

2.0 star property
10.0 out of 10, Exceptional, (1)
"I'd like to say that upon arriving the house was beautiful. There's a gorgeous backyard pond with a water spout in the middle. A nice accessible driveway and a cute little cobblestone walkway leading up to the entrance of the guest house. It was beautiful when we arrived inside. House was clean and inviting and there was also cold water and refreshments. Will 100% be booking again... I would give it a hundred stars if I could. Best experience ever."
Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

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 AU$504
includes taxes & fees
31 July - 1 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.0 out of 10, (11)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

10.0 out of 10, Exceptional, (1)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
The price is AU$814
includes taxes & fees
28 July - 29 July
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

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 AU$256
includes taxes & fees
28 July - 29 July
HOMEY HOMEY

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.0 out of 10, Wonderful, (6)
"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "
The price is AU$250
includes taxes & fees
3 Aug - 4 Aug
Totally Private Cozy studio in awesome Hartford with WiFi, AC

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (8)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Modern Condo|DWNTN Hartord| XL Center| GYM

4.0 out of 10, (2)
"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 AU$324
includes taxes & fees
28 July - 29 July
Modern Condo|DWNTN Hartord| XL Center| GYM

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is AU$562
includes taxes & fees
10 Aug - 11 Aug
Big farmhouse in the foothills of the Berkshires

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (30)
"We had the best time with the farm animals, great pool and unbelievable views"
Mountaintop Horse Farm with Heated Pool

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

2.0 star property
6.6 out of 10, (4)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (14)
"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!

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (8)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .
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

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 SS&C SummerWind Performing 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.