Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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

9.4 out of 10, Exceptional, (13)
"I had such a good time here that I actually added three more weeks so this is the first of three reviews as I booked them separately. The host was really nice working with me and the associate that supports any household requests as well. Everything works perfectly, but the host associate was nice to come and anticipate the batteries on the smart lock would be running low and came and changed them along with leaving me extra snow melt, and a shovel after clearing the walkways. The house is well...
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
A “Wow” Experience everywhere there is something to stimulate your mind Interest

Island Vibes Home

9.8 out of 10, Exceptional, (13)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home

PICON COZY

7.6 out of 10, Good, (57)
"I booked this for my elderly Mom and her adult granddaughter who were in town for the holidays and also awaiting a January 1 move in to a new apartment. Fidelis was attentive, kind, and responded quickly to any issues in the property. The place itself was truly like home away from home and convenient to stores, shopping and public transportation. I would recommend anyone looking for a cozy stay in Springfield to check it out. It is well worth the price. I would even say it is a bargain and...
The price is €167
includes taxes & fees
23 Feb - 24 Feb
PICON COZY

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (11)
"We came for the night and the location was perfect. In walking distance to bars and restaurants. Clean, easy, no complaints. If there is a game/event at the XL Center then you should know that on-street parking may be difficult. This isn't a problem, just something to be aware of."
The price is €189
includes taxes & fees
21 Feb - 22 Feb
Lux Boutique Large Private LOFT Pratt St Hartford

The Skyway

The price is €303
includes taxes & fees
25 Feb - 26 Feb
The Skyway

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is €376
includes taxes & fees
16 Mar - 17 Mar
Blue Back Bungalow

Totally Private Cozy studio in awesome Hartford with WiFi, AC

The price is €175
includes taxes & fees
21 Feb - 22 Feb
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Cozy 4 Bedroom West Hartford House

2.0 star property
9.0 out of 10, Wonderful, (2)
"Convenient. Clean. Very comfortable beds."
Cozy 4 Bedroom West Hartford House

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (57)
"More than expected, owner pays attention to detail, many amenities, spotless. All the comforts of home. Owner very prompt to answer any questions. Will definitely be booking this againRobbin and Rich Willis"
Linny's Updated Lakeview Cottage - Cozy & Modern

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor

Cozy BoHo pet & family friendly near downtown & hospitals

8.4 out of 10, Very good, (7)
"We stayed 4 nights for our family trip. The home was sparkling clean and we found all we need. I love boho styled rooms. No issues with neighbors. All kind of TV subscription available. Overall very positive experience. Thank you!"
The price is €272
includes taxes & fees
26 Feb - 27 Feb
Cozy BoHo pet & family friendly near downtown & hospitals

Charming Cottage by the Lake❤️

9.6 out of 10, Exceptional, (8)
"Very cozy little home. "
Charming Cottage by the Lake❤️

Lovely 1-bedroom third floor apartment in Hartford with fast WiFi access

Lovely 1-bedroom third floor apartment in Hartford with fast WiFi access

Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

9.8 out of 10, Exceptional, (115)
"Beautiful house, sitting high and overlooking the Connecticut River. Can't imagine a more beautiful setting. Very large kitchen, great for cooking in with friends. Even has an adjacent helicopter pad (although it's $4k to go from Hartford airport to the house, 1-way!). Had a great time."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

Historical Blvd. Cheney Bros HillTop Mansion

9.0 out of 10, Wonderful, (12)
"My parents really loved their stay."
Historical Blvd. Cheney Bros HillTop Mansion

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (6)
"We loved everything about this home! It fit us perfectly and we would love to rent it again!"
Historic Farmhouse Near Mountains & Colleges!

The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

9.6 out of 10, Exceptional, (8)
"We had a great time at Highland Lake. The apartment was so comfortable, and larger than I would have thought from the description. It was convenient to town - the teens loved access to DQ, pizza shops, etc just a few minutes away. There were kayaks and a paddleboat we could borrow, which I somehow missed in the description - nice pluses! The lake access from the dock was perfect. We brought stand-up paddleboards, and had an easy time launching them and exploring the lake. In the apartment,...
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

WeHa Oak Haven

10.0 out of 10, Exceptional, (3)
"The property is a townhome that is very easy to find and very accessible to the main highway to get anywhere you need easily. It is also located near a couple very good restaurants within walking distance that I would highly suggest, Iron Works and Effies Diner. It was perfect for the two of us for the week. Thank you!"
WeHa Oak Haven

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

9.6 out of 10, Exceptional, (7)
"This property was exactly what we needed. Perfect location beautiful house very clean and very comfortable. We will definitely return "
The price is €318
includes taxes & fees
27 Feb - 28 Feb
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins 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.
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Other types of properties in Windsor you may be interested in

HYATT house Hartford North/Windsor

3.0 star property
9.0 out of 10, Wonderful, (1003)
"The overall experience was good."
The price is €111
includes taxes & fees
6 Mar - 7 Mar
HYATT house Hartford North/Windsor

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3.0 star property
8.8 out of 10, Excellent, (1002)
"Perfecto "
The price is €111
includes taxes & fees
28 Feb - 1 Mar
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Marriott Hartford/Windsor Airport

3.5 star property
8.4 out of 10, Very good, (1002)
"Tjis hotel hosted the coronation for the Imperial Sovereign Court of CT and has for 19 years. The service, attentiveness, and quality never faulters. Loved staying hear. It is well ran and well maintained. Biggest appreciation to Enita the bartender, and the shuttle drivers, Frank and John. Even in the middle of a snow storm, this was a warm, inviting space!"
The price is €175
includes taxes & fees
28 Feb - 1 Mar
Marriott Hartford/Windsor Airport
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.

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?

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 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 Windsor Historical Society and Vintage Radio and Communications Museum of Connecticut.

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.