A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windsor vacation rentals

A spacious kitchen with wooden cabinets, a large island, and a dining area with chairs and a rug.

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 reviews)
"The place is easy to locate. It is as beautiful as the photo. Clean and spacious.I definitely would stay there again."
United States
Delores N.
$529 nightly
The price is $603
Sep 30 - Oct 1
Total with taxes and fees
Spacious Yard w/ Gazebo: Charming Windsor Retreat
A modern living room with a sofa, a coffee table, and a rug.

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
$106 nightly
The price is $119
Oct 5 - Oct 6
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
A bedroom with a bed, two bedside lamps, a nightstand, a dresser, and artwork on the wall.

3. Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester

Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (18 reviews)
"Great place"
United States
Jason
$186 nightly
The price is $211
Sep 30 - Oct 1
Total with taxes and fees
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
A blue sofa with plaid pillows, a glass coffee table with a white flower centerpiece, and two potted plants.

4. 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.
$231 nightly
The price is $248
Sep 30 - Oct 1
Total with taxes and fees
Premier League Pad - with Free Parking, Heat & AC
A kitchen with wooden shelves, a toaster, and a sink.

5. 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
9.6 out of 10, Exceptional, (28 reviews)
"Great stay and location for a single traveler with a dog! Owners were good communicators. Would stay again!"
United States
Nicole G.
$153 nightly
The price is $173
Oct 4 - Oct 5
Total with taxes and fees
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
A wooden deck with a staircase leading to a covered area with chairs.

6. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (6 reviews)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
Oct 1 - Oct 2
Total with taxes and fees
Humble Abode #2
A living room with a dining area, a TV, and a large window with a view of buildings.

7. 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
$204 nightly
The price is $217
Oct 5 - Oct 6
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
A living room with a TV, sofas, armchairs, and a fireplace.

8. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
$394 nightly
The price is $464
Oct 7 - Oct 8
Total with taxes and fees
Willow Haven 2BR Cozy Retreat, Close to Hartford
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

Crested One Place - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (1 review)
"Perfect place for a quick stay"
United States
phillip s.
$210 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
Crested One Place - with Free Parking, Heat & AC
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

10. 2 Queen Beds|Non-Smoking,Micfridge

2 Queen Beds|Non-Smoking,Micfridge
Enfield
10.0 out of 10, Exceptional, (4 reviews)
"Quick stop but comfy bed. Close to the highway made it easy to find."
United States
Anonymous traveler
$80 nightly
The price is $92
Oct 16 - Oct 17
Total with taxes and fees
2 Queen Beds|Non-Smoking,Micfridge
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

11. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
$259 nightly
The price is $295
Sep 30 - Oct 1
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
A living room with a sectional sofa, a coffee table, a dining table with chairs, and a window with curtains.

12. Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
Manchester
$203 nightly
The price is $231
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

13. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (16 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
$270 nightly
The price is $291
Oct 5 - Oct 6
Total with taxes and fees
The Serene Skyway Retreat
A bedroom with a bed, a round table, a grey sofa, a window with a view of buildings, and a wooden wardrobe.

14. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
$239 nightly
The price is $274
Sep 30 - Oct 1
Total with taxes and fees
Trumbull Apartments
A wooden deck with a railing, a door, and a view of trees.

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

Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
Manchester Center
9.8 out of 10, Exceptional, (15 reviews)
"Nice private place to stay."
United States
Brian A.
$150 nightly
The price is $170
Oct 3 - Oct 4
Total with taxes and fees
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
A modern dining area with a marble table, white chairs, and a chandelier.

16. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"House was great for our family stay!"
United States
Kim A.
$260 nightly
The price is $296
Sep 30 - Oct 1
Total with taxes and fees
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
A bedroom with a bed, bedside tables, a nightstand, and a patterned rug.

17. Premium Enjoyable 1-bedroom apartment in central Manchester

Premium Enjoyable 1-bedroom apartment in central Manchester
Manchester
$183 nightly
The price is $207
Oct 5 - Oct 6
Total with taxes and fees
Premium Enjoyable 1-bedroom apartment in central Manchester
A covered porch with wicker furniture, a potted plant, and a small table.

18. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (20 reviews)
"The bungalow is in a great location - close to I84 and West Hartford center. The kitchen had a lot of great appliances to make cooking easy. The coffee pot was a Keurig/carafe combo - which we really liked. We enjoyed drinking our morning coffee on the front porch. We would definitely stay her again!"
United States
Ben
$284 nightly
The price is $302
Oct 14 - Oct 15
Total with taxes and fees
The Blue Back Bungalow
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.

19. TruStay in Central CT

TruStay in Central CT
Manchester
10.0 out of 10, Exceptional, (1 review)
"The apartment was immaculate. Everything new, Very comfortable."
United States
Maxine L.
$223 nightly
The price is $238
Oct 26 - Oct 27
Total with taxes and fees
TruStay in Central CT
A bedroom with a bed, a ceiling fan, a nightstand with a lamp, a chair with a pillow, and a window with curtains.

20. Location, is the key for this 3 bedroom!

Location, is the key for this 3 bedroom!
Frog Hollow
9.4 out of 10, Exceptional, (8 reviews)
"My family and I had a great stay . Taz was a great host and was prompt anytime I had a question. Space was clean and spacious . Will definitely book again when we come back in town!"
United States
Kaneisha O.
$363 nightly
The price is $414
Sep 30 - Oct 1
Total with taxes and fees
Location, is the key for this 3 bedroom!
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

Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"The staff was great and everything was very clean."
James 1-night trip
Posted 1 hour ago
Blue A Modern Hotel, an Ascend Collection Hotel

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $234 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.