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

Our top choices for Windsor holiday 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, (12 reviews)
"Very clean and spacious! Would definitely recommend."
United States
Husam
The price is AU$174
includes taxes & fees
18 Oct - 19 Oct
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
The price is AU$534
includes taxes & fees
11 Oct - 12 Oct
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.
The price is AU$742
includes taxes & fees
20 Oct - 21 Oct
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
The price is AU$309
includes taxes & fees
11 Oct - 12 Oct
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.
The price is AU$252
includes taxes & fees
11 Oct - 12 Oct
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
The price is AU$324
includes taxes & fees
14 Oct - 15 Oct
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.
The price is AU$665
includes taxes & fees
12 Oct - 13 Oct
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.
The price is AU$442
includes taxes & fees
2 Nov - 3 Nov
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
The price is AU$229
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AU$620
includes taxes & fees
19 Oct - 20 Oct
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.
The price is AU$370
includes taxes & fees
25 Oct - 26 Oct
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.
The price is AU$583
includes taxes & fees
14 Oct - 15 Oct
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.
The price is AU$632
includes taxes & fees
14 Oct - 15 Oct
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.
The price is AU$326
includes taxes & fees
26 Oct - 27 Oct
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
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
The price is AU$436
includes taxes & fees
14 Oct - 15 Oct
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.
The price is AU$446
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AU$610
includes taxes & fees
13 Oct - 14 Oct
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, (17 reviews)
"Nice private place to stay."
United States
Brian A.
The price is AU$246
includes taxes & fees
26 Oct - 27 Oct
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
The price is AU$743
includes taxes & fees
13 Oct - 14 Oct
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"NA"
Willie L 2-night trip
Posted 6 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

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$111 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?

Cabin Love at the Lake: This holiday home rental outside of Windsor offers a fireplace, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Windsor?

Expedia has 9 holiday 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 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.