A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Rentals

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

Cabin Love at the Lake : This vacation home rental outside of Windsor offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Dates

November 2026

December 2026

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Our top choices for Windsor vacation rentals

A garden pathway leading to a white arbor with pink flowers, surrounded by lush greenery and a clear sky.

1. Windsor Retreat | Near Hartford & UConn College

Windsor

Delores N.

￥110,477 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a sofa, a coffee table, and a rug.

2. Entire guest suite in South Windsor, Connecticut

South Windsor

Arthur

￥17,675 total

includes taxes & fees

Nov 16 - Nov 17

A reception area with a counter, a plant, and an exit sign.

3. 1 Queen Bed | Micfridge

Windsor Locks

Anonymous traveler

￥14,200 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a bed, a desk, a chair, a window with curtains, and a wall-mounted lamp.

4. 1 Queen Bed | ADA/Tub/Micfridge

Windsor Locks

Anonymous traveler

￥14,200 total

includes taxes & fees

Nov 15 - Nov 16

A modern bedroom with a large bed, a wooden wardrobe, a small round table, and a window with blinds.

5. Modern Private Furnished Studio Downtown Hartford

Downtown Hartford

Lynnett

￥29,244 total

includes taxes & fees

Nov 13 - Nov 14

A multi-story building with a brick facade, large windows, and a street lamp.

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

Downtown Hartford

Bonita T.

￥33,094 total

includes taxes & fees

Nov 15 - Nov 16

A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

7. 1 King Bed|Smoking, Micfridge

Enfield

￥12,422 total

includes taxes & fees

Nov 15 - Nov 16

A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

8. The Serene Skyway Retreat

Windsor Locks

Michael P.

￥45,314 total

includes taxes & fees

Nov 30 - Dec 1

A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

9. Crested One Place - with Free Parking, Heat & AC

Manchester

phillip s.

￥33,679 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a dining area, a TV, and a large window with a view of buildings.

10. Central Chic Pad - with Free Parking, Heat & AC

Manchester

Domenic

￥33,679 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a central island, stainless steel appliances, and black cabinets.

11. Fully Furnished Private Apartment, Elevator, Wi-Fi A/C

Downtown Hartford

Shea O.

￥35,236 total

includes taxes & fees

Nov 16 - Nov 17

A hotel reception area with a receptionist, a guest, and a child.

12. 1 Queen Bed | Wethersfield

Wethersfield

Anonymous traveler

￥13,308 total

includes taxes & fees

Nov 15 - Nov 16

A kitchen cabinet with shelves holding glasses, bowls, and plates.

13. Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay

Manchester

￥35,158 total

includes taxes & fees

Nov 20 - Nov 21

A modern living room with a gray sofa, a coffee table, and a dining area with a table and chairs. There is a TV and a plant in the room.

14. TruStay in Central CT

Manchester

Maxine L.

￥37,196 total

includes taxes & fees

Nov 15 - Nov 16

15. 1 Queen Bed | Deluxe, Micfridge

Windsor Locks

Anonymous traveler

￥14,200 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with black cabinets, a white countertop, and a built-in oven.

16. Lux Boutique Large Private LOFT Pratt St Hartford

Downtown Hartford

Josh H.

￥41,942 total

includes taxes & fees

Nov 15 - Nov 16

A kitchen with wooden shelves, a toaster, and a sink.

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

East Windsor

"The interior is exactly as the photos showed. Kudos to the interior design. The unit itself is on the 1st floor of a 2 story building, situated next to the street. The traffic slows down at night so one doesn't get bothered by the noise. We have a parking area right in front of the unit. We can hear the upstairs traffic but it's not constant. The bathroom is very small. The unit has low ceiling so it may not be suited for very tall people. It is a compact unit, but it has very thing we...

Tom

￥26,218 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with a railing, a door, and a view of trees.

18. Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

Manchester Center

Brian A.

￥25,634 total

includes taxes & fees

Nov 16 - Nov 17

A covered porch with wicker furniture, a potted plant, and a small table.

19. The Blue Back Bungalow

West Hartford

James K.

￥47,278 total

includes taxes & fees

Nov 19 - Nov 20

20. 1 Queen Bed | Smoking

Wethersfield

Anonymous traveler

￥13,308 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Windsor Hotel Reviews

An outdoor dining area with tables and chairs, surrounded by plants and trees.

Delamar West Hartford

West Hartford

10/10 Excellent

elizabeth

A hotel patio with outdoor seating, a fire pit, and a building with multiple floors and large windows.

Cambria Hotel Manchester South Windsor

South Windsor

10/10 Excellent

LaToya

A modern hotel room with a dining area, seating arrangements, and a large TV screen.

Hampton Inn Hartford/Airport

Windsor

10/10 Excellent

Jeffrey S

A modern kitchen with a central island, bar stools, and pendant lighting.

HYATT house Hartford North/Windsor

Windsor

10/10 Excellent

James

A modern living room with a fireplace, comfortable seating, and a flat-screen TV mounted above the fireplace.

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Windsor

10/10 Excellent

Jeffrey

A modern hotel room with a sofa, armchair, and a TV mounted on the wall.

Courtyard By Marriott Hartford/Windsor Airport

Windsor

10/10 Excellent

My husband and daughter and I arrived VERY late--2 am--and Jerrell the night clerk got us checked in quickly and courteously while at the same time fielding a phone call from someone who was obviously giving him a hard time--yet he remained calm, pleasant, and professional. We really appreciated his professionalism and courtesy as well as that of the breakfast staff the next morning. The beds and pillows were comfortable and the room clean as one would expect from a Marriott. Note: there are 2...

Chicago travele

A large, historic building with a covered porch and outdoor seating area.

Simsbury 1820 House

Simsbury Center

10/10 Excellent

Warren

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped driveway.

Holiday Inn Express & Suites Bradley Airport by IHG

Windsor Locks

10/10 Excellent

Chad

An outdoor patio area with a fire pit, seating, and umbrellas.

Hampton Inn & Suites Rocky Hill - Hartford South

Rocky Hill

10/10 Excellent

Christopher

A hot tub with a tiled edge and a metal ladder, surrounded by large windows with a view of a parking lot and trees.

Hampton Inn Springfield South Enfield

Enfield

10/10 Excellent

Chastity

A Hampton Inn & Suites with a brick facade, large windows, and a well-lit entrance.

Hampton Inn & Suites Hartford/East Hartford

East Hartford

10/10 Excellent

Tom

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:

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Frequently Asked Questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals in Windsor close to Windsor Arts Center, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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?

Cabin Love at the Lake: This vacation home rental outside of Windsor offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Windsor?

Expedia has 9 vacation rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Historical Society 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 Arts Center.

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.

Windsor Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor vacation rentals

1. Windsor Retreat | Near Hartford & UConn College

2. Entire guest suite in South Windsor, Connecticut

3. 1 Queen Bed | Micfridge

4. 1 Queen Bed | ADA/Tub/Micfridge

5. Modern Private Furnished Studio Downtown Hartford

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

7. 1 King Bed|Smoking, Micfridge

8. The Serene Skyway Retreat

9. Crested One Place - with Free Parking, Heat & AC

10. Central Chic Pad - with Free Parking, Heat & AC

11. Fully Furnished Private Apartment, Elevator, Wi-Fi A/C

12. 1 Queen Bed | Wethersfield

13. Perfect comfort 1-bedroom apartment in welcoming Manchester for your stay

14. TruStay in Central CT

15. 1 Queen Bed | Deluxe, Micfridge

16. Lux Boutique Large Private LOFT Pratt St Hartford

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

18. Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

19. The Blue Back Bungalow

20. 1 Queen Bed | Smoking

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Delamar West Hartford

10/10 Excellent

Find out more about Windsor

Frequently Asked Questions

Can I find vacation rentals in Windsor?

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

How many vacation rentals are there in Windsor?

What can I see and do in Windsor?

What are vacation rentals like in Windsor?