Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Windsor vacation rentals

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, (39 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is ￥16,980
￥41,695 total
includes taxes & fees
Feb 10 - Feb 11
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior

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

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (36 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 ￥16,854
￥41,707 total
includes taxes & fees
Feb 9 - Feb 10
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
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, (48 reviews)
"It was great! Thank you :-) "
United States
Becki S.
The price is ￥20,659
￥46,083 total
includes taxes & fees
Feb 17 - Feb 18
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Smart TV, computer monitors

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is ￥13,560
￥33,046 total
includes taxes & fees
Feb 23 - Feb 24
Central Chic Pad - with Free Parking, Heat & AC
Fridge, microwave, stovetop, coffee/tea maker

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (11 reviews)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
The price is ￥10,612
￥44,788 total
includes taxes & fees
Feb 11 - Feb 12
Charming Luxury 1BR Near Downtown. Dog Friendly!
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is ￥13,584
￥18,766 total
includes taxes & fees
Feb 8 - Feb 9
Entire guest suite in South Windsor, Connecticut
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is ￥19,024
￥44,517 total
includes taxes & fees
Feb 8 - Feb 9
Modern & Cozy Cape | 4 Bedroom House | Central Location
Fridge, microwave, stovetop, coffee/tea maker

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

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
East Windsor
10.0 out of 10, Exceptional, (21 reviews)
"Clean place, simple check in, over great!"
United States
Allison S.
The price is ￥20,942
￥27,228 total
includes taxes & fees
Feb 8 - Feb 9
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Interior

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (6 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is ￥18,814
￥31,082 total
includes taxes & fees
Mar 9 - Mar 10
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12 reviews)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is ￥13,326
￥44,392 total
includes taxes & fees
Feb 9 - Feb 10
The Serene Skyway Retreat
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is ￥18,814
￥36,060 total
includes taxes & fees
Feb 9 - Feb 10
Family Stays: Middletown, CT
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is ￥22,890
￥51,879 total
includes taxes & fees
Feb 22 - Feb 23
#24 *Serenity* A Lakefront Cottage Retreat
1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
The price is ￥14,131
￥31,343 total
includes taxes & fees
Feb 8 - Feb 9
#2 *Beautiful 1 BR Apartment - Central CT*
Smart TV

Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
The price is ￥17,669
￥38,193 total
includes taxes & fees
Feb 24 - Feb 25
Premier League Pad - with Free Parking, Heat & AC
Terrace/patio

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is ￥19,102
￥50,071 total
includes taxes & fees
Feb 9 - Feb 10
Soothing 2-bedroom lower-level apartment in Berlin
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is ￥14,675
￥29,027 total
includes taxes & fees
Feb 9 - Feb 10
Peaceful Meadow Retreat
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, (16 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is ￥18,709
￥43,998 total
includes taxes & fees
Feb 16 - Feb 17
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is ￥21,854
￥42,112 total
includes taxes & fees
Feb 13 - Feb 14
#26 Beautifully Renovated 2 BR Home
Smart TV

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is ￥13,522
￥32,953 total
includes taxes & fees
Feb 23 - Feb 24
Crested One Place - with Free Parking, Heat & AC
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is ￥23,206
￥33,762 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Guest Suite in Historic Home
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Overall great stay. Staff was friendly and helpful, room was clean, breakfast was nice, and the gym was well taken care of. We had loud neighbors one night, but we called the desk and the helped us out instantly. Overall, we felt very comfortable here. "
Juan 2-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG

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 vacation rentals in Windsor?

Yes, there are vacation rentals close to popular points of interest in Windsor, or you can select a more secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What's the top vacation rental that Windsor has to offer?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation home rental outside of Windsor offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Windsor?

Expedia has 7 vacation 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 Vintage Radio and Communications Museum of Connecticut.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.