A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windsor vacation rentals

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

1. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (11 reviews)
"Good location"
United States
Arthur
$106 nightly
The price is $119
Oct 11 - Oct 12
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
A multi-story building with a brick facade, large windows, and a storefront with signage.

2. 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
$325 nightly
The price is $373
Oct 7 - Oct 8
Total with taxes and fees
Trumbull Apartments
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a coffee maker on the table.

3. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
10.0 out of 10, Exceptional, (12 reviews)
"Great stay, home was comfortable and communication w owner was very smooth!"
United States
Stacey P.
$467 nightly
The price is $529
Oct 20 - Oct 21
Total with taxes and fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A bedroom with a bed, two bedside lamps, a nightstand, a dresser, and artwork on the wall.

4. 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
$188 nightly
The price is $213
Oct 7 - Oct 8
Total with taxes and fees
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
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 11 - Oct 12
Total with taxes and fees
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
A living room with a dining area, a TV, and a large window with a view of buildings.

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

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.4 out of 10, Exceptional, (8 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
$208 nightly
The price is $221
Oct 7 - Oct 8
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
Dining

7. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (25 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
$439 nightly
The price is $474
Oct 12 - Oct 13
Total with taxes and fees
Prime West Hartford Center: Timeless Charm
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

8. 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.
$270 nightly
The price is $306
Oct 8 - Oct 9
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
A wooden deck with a staircase leading to a covered area with chairs.

9. 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 11 - Oct 12
Total with taxes and fees
Humble Abode #2
A bedroom with a bed, a ceiling fan, a nightstand with a lamp, a chair with a pillow, and a window with curtains.

10. 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.
$387 nightly
The price is $438
Oct 7 - Oct 8
Total with taxes and fees
Location, is the key for this 3 bedroom!
A blue sofa with plaid pillows, a glass coffee table with a white flower centerpiece, and two potted plants.

11. 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.
$238 nightly
The price is $255
Oct 7 - Oct 8
Total with taxes and fees
Premier League Pad - with Free Parking, Heat & AC
A spacious living room with hardwood flooring, a grey sofa, a coffee table, and a chandelier.

12. West Hartford Center: Charming New England Apt

West Hartford Center: Charming New England Apt
West Hartford
10.0 out of 10, Exceptional, (9 reviews)
"Immaculate, nice decor, very comfortable beds, every detail is well thought out. "
United States
Cathryna B.
$396 nightly
The price is $429
Oct 7 - Oct 8
Total with taxes and fees
West Hartford Center: Charming New England Apt
A porch with a table and chairs, an American flag, and a hanging flower basket.

13. West Hartford Center: Cozy New England Apartment

West Hartford Center: Cozy New England Apartment
West Hartford
10.0 out of 10, Exceptional, (12 reviews)
"Great comfortable spot- great location!"
United States
Sara H.
$396 nightly
The price is $429
Oct 7 - Oct 8
Total with taxes and fees
West Hartford Center: Cozy New England Apartment
A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

14. 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 27 - Oct 28
Total with taxes and fees
Crested One Place - with Free Parking, Heat & AC
A covered patio with a dining table, chairs, and a grill.

15. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (36 reviews)
"We loved being so close to downtown West Hartford. The house had everything we needed for a fun graduation weekend."
United States
Trish
$539 nightly
The price is $587
Oct 8 - Oct 9
Total with taxes and fees
Prime West Hartford Center Location: Historic Gem
A covered porch with wicker furniture, a potted plant, and a small table.

16. 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
$292 nightly
The price is $309
Oct 14 - Oct 15
Total with taxes and fees
The Blue Back Bungalow
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

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

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
$273 nightly
The price is $309
Nov 1 - Nov 2
Total with taxes and fees
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A living room with a blue sofa, a round coffee table, and a staircase.

18. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
$412 nightly
The price is $443
Oct 13 - Oct 14
Total with taxes and fees
The Game House Arcade – West Hartford
A wooden deck with a railing, a door, and a view of trees.

19. 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
9.6 out of 10, Exceptional, (16 reviews)
"Nice private place to stay."
United States
Brian A.
$150 nightly
The price is $170
Oct 18 - Oct 19
Total with taxes and fees
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

20. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
$537 nightly
The price is $584
Oct 13 - Oct 14
Total with taxes and fees
Charming New England Home in West Hartford Center
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

Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

10/10 Excellent
"Great price for the stay highly recommend"
John 1-night trip
Posted 1 hour ago
Motel 6 Enfield, CT - Hartford

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 $78 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.