A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Windsor vacation rentals

Dining

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.
$636 nightly
The price is $720
Sep 1 - Sep 2
Total with taxes and fees
Spacious Yard w/ Gazebo: Charming Windsor Retreat
Smart TV

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
$121 nightly
The price is $136
Aug 17 - Aug 18
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
Smart TV, offices, computer monitors

3. 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
$200 nightly
The price is $214
Aug 31 - Sep 1
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
Coffee/tea maker, fridge, microwave, stovetop

4. 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
9.8 out of 10, Exceptional, (27 reviews)
"I would absolutely stay here again. It's perfectly located for seeing a show at Broad Brook Opera House. Parking and check in couldn't be easier. The room has everything you need for a very comfortable stay."
United States
Anthony
$153 nightly
The price is $173
Aug 19 - Aug 20
Total with taxes and fees
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Smart TV, fireplace

5. 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.
$316 nightly
The price is $343
Aug 12 - Aug 13
Total with taxes and fees
The Serene Skyway Retreat
Smart TV, offices

6. 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.
$199 nightly
The price is $212
Aug 30 - Aug 31
Total with taxes and fees
Crested One Place - with Free Parking, Heat & AC
TV, fireplace

7. 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
$338 nightly
The price is $397
Aug 12 - Aug 13
Total with taxes and fees
Willow Haven 2BR Cozy Retreat, Close to Hartford
Living area

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

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
Manchester
$239 nightly
The price is $271
Aug 12 - Aug 13
Total with taxes and fees
Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
1 bedroom, desk, iron/ironing board, WiFi (free)

9. 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, (14 reviews)
"Great place"
United States
Jason
$190 nightly
The price is $215
Aug 12 - Aug 13
Total with taxes and fees
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
Smart TV, offices

10. 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.
$229 nightly
The price is $246
Aug 16 - Aug 17
Total with taxes and fees
Premier League Pad - with Free Parking, Heat & AC
Property grounds

11. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
$145 nightly
The price is $164
Aug 17 - Aug 18
Total with taxes and fees
Humble Abode #2
Smart TV, offices, computer monitors

12. 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.
$221 nightly
The price is $236
Aug 18 - Aug 19
Total with taxes and fees
TruStay in Central CT
Property grounds

13. 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
10.0 out of 10, Exceptional, (9 reviews)
"Nice private place to stay."
United States
Brian A.
$137 nightly
The price is $155
Aug 22 - Aug 23
Total with taxes and fees
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
Terrace/patio

14. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (19 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
$318 nightly
The price is $339
Aug 12 - Aug 13
Total with taxes and fees
The Blue Back Bungalow
Coffee/tea maker, fridge, microwave, oven

15. 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
9.8 out of 10, Exceptional, (10 reviews)
"Super easy effective rental. Everything was clean and meet everyone one of our needs!"
United States
Matthew R.
$397 nightly
The price is $449
Aug 25 - Aug 26
Total with taxes and fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Dining

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

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"House was great for our family stay!"
United States
Kim A.
$285 nightly
The price is $322
Aug 12 - Aug 13
Total with taxes and fees
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Interior

17. 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.
$263 nightly
The price is $298
Aug 31 - Sep 1
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV

18. 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, (27 reviews)
"Was a great stay"
United States
John S.
$286 nightly
The price is $324
Aug 31 - Sep 1
Total with taxes and fees
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
3 bedrooms, WiFi (free)

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

Location, is the key for this 3 bedroom!
Frog Hollow
9.6 out of 10, Exceptional, (7 reviews)
"It was nice and close to where we had a wedding. Plenty of room for us all. Host was very easy to contact. "
United States
Shawn R.
$432 nightly
The price is $490
Sep 11 - Sep 12
Total with taxes and fees
Location, is the key for this 3 bedroom!
Interior

20. The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
$269 nightly
The price is $287
Aug 18 - Aug 19
Total with taxes and fees
The Historic Hideaway
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

8/10 Good
"It was ok a little dated breakfast was pretty good coffee was excellent ..."
Mickey 2-night trip
Posted 3 hours ago
Holiday Inn Express Southington by IHG

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 $298 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?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This highly rated vacation home rental in Windsor has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Historical Society and Vintage Radio and Communications Museum of Connecticut, whereas Keney Park and Northwest Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Windsor Arts Center and Loomis Chaffee School.

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.