A rustic barn surrounded by autumn foliage and a field.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor holiday 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.
The price is AU$1,016
includes taxes & fees
1 Sept - 2 Sept
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
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
The price is AU$184
includes taxes & fees
8 Sept - 9 Sept
Entire guest suite in South Windsor, Connecticut
A living room with a dining area, a TV, and a large window with a view of buildings.

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
The price is AU$296
includes taxes & fees
16 Sept - 17 Sept
Central Chic Pad - with Free Parking, Heat & AC
A kitchen with wooden shelves, a toaster, and a sink.

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
9.6 out of 10, Exceptional, (28 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
The price is AU$244
includes taxes & fees
30 Aug - 31 Aug
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

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.
The price is AU$473
includes taxes & fees
31 Aug - 1 Sept
The Serene Skyway Retreat
A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

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.
Crested One Place - with Free Parking, Heat & AC
A blue sofa with plaid pillows, a glass coffee table with a white flower centerpiece, and two potted plants.

7. 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 AU$340
includes taxes & fees
30 Aug - 31 Aug
Premier League Pad - with Free Parking, Heat & AC
A wooden deck with a railing, a door, and a view of trees.

8. 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, (11 reviews)
"Nice private place to stay."
United States
Brian A.
The price is AU$219
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
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, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is AU$232
includes taxes & fees
15 Sept - 16 Sept
Humble Abode #2
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.

10. 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.
The price is AU$330
includes taxes & fees
30 Aug - 31 Aug
TruStay in Central CT
A living room with a sectional sofa, a coffee table, a dining table with chairs, and a window with curtains.

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

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
Manchester
The price is AU$374
includes taxes & fees
30 Aug - 31 Aug
Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking
A covered porch with wicker furniture, a potted plant, and a small table.

12. 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
The price is AU$449
includes taxes & fees
26 Aug - 27 Aug
The Blue Back Bungalow
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

13. 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.
The price is AU$410
includes taxes & fees
31 Aug - 1 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
A bedroom with a bed, two bedside lamps, a nightstand, a dresser, and artwork on the wall.

14. 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, (16 reviews)
"Great place"
United States
Jason
The price is AU$298
includes taxes & fees
8 Sept - 9 Sept
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
A living room with a TV, sofas, armchairs, and a fireplace.

15. 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
The price is AU$557
includes taxes & fees
1 Sept - 2 Sept
Willow Haven 2BR Cozy Retreat, Close to Hartford
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

16. 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, (29 reviews)
"Was a great stay"
United States
John S.
The price is AU$451
includes taxes & fees
20 Sept - 21 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

17. 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.
The price is AU$385
includes taxes & fees
31 Aug - 1 Sept
The Historic Hideaway
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.

18. 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, (11 reviews)
"Super easy effective rental. Everything was clean and meet everyone one of our needs!"
United States
Matthew R.
The price is AU$719
includes taxes & fees
8 Sept - 9 Sept
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A bedroom with a bed, a ceiling fan, a nightstand with a lamp, a chair with a pillow, and a window with curtains.

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.
The price is AU$634
includes taxes & fees
8 Sept - 9 Sept
Location, is the key for this 3 bedroom!
A spacious living room with hardwood flooring, a grey sofa, a coffee table, and a chandelier.

20. West Hartford Center: Charming New England Apt

West Hartford Center: Charming New England Apt
West Hartford
10.0 out of 10, Exceptional, (8 reviews)
"Immaculate, nice decor, very comfortable beds, every detail is well thought out. "
United States
Cathryna B.
The price is AU$589
includes taxes & fees
26 Aug - 27 Aug
West Hartford Center: Charming New England Apt
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

Baymont by Wyndham East Windsor Bradley Airport

Baymont by Wyndham East Windsor Bradley Airport

8/10 Good
"My stay at this property was very good"
Russell 7-night trip
Posted 2 hours ago
Baymont by Wyndham East Windsor Bradley Airport

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$219 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Windsor Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What are some of the best holiday rentals that Windsor has to offer?

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

How many holiday rentals are there in Windsor?

Expedia has 7 holiday rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society, 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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.