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

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.
The price is SAR 1,232
SAR 2,723 total
includes taxes & fees
11 Sep - 12 Sep
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
The price is SAR 378
SAR 510 total
includes taxes & fees
17 Aug - 18 Aug
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
The price is SAR 328
SAR 802 total
includes taxes & fees
31 Aug - 1 Sep
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
The price is SAR 500
SAR 650 total
includes taxes & fees
23 Aug - 24 Aug
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.
The price is SAR 511
SAR 1,337 total
includes taxes & fees
18 Aug - 19 Aug
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.
The price is SAR 324
SAR 797 total
includes taxes & fees
30 Aug - 31 Aug
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
The price is SAR 368
SAR 1,519 total
includes taxes & fees
13 Aug - 14 Aug
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
The price is SAR 485
SAR 1,012 total
includes taxes & fees
11 Sep - 12 Sep
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
The price is SAR 473
SAR 807 total
includes taxes & fees
13 Aug - 14 Aug
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.
The price is SAR 423
SAR 926 total
includes taxes & fees
10 Sep - 11 Sep
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
The price is SAR 469
SAR 615 total
includes taxes & fees
17 Aug - 18 Aug
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.
The price is SAR 393
SAR 887 total
includes taxes & fees
18 Aug - 19 Aug
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.
The price is SAR 488
SAR 636 total
includes taxes & fees
17 Aug - 18 Aug
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
The price is SAR 379
SAR 1,286 total
includes taxes & fees
16 Aug - 17 Aug
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.
The price is SAR 703
SAR 1,687 total
includes taxes & fees
25 Aug - 26 Aug
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.
The price is SAR 559
SAR 1,210 total
includes taxes & fees
13 Aug - 14 Aug
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.
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.
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.
The price is SAR 860
SAR 1,937 total
includes taxes & fees
9 Sep - 10 Sep
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.
The price is SAR 319
SAR 1,078 total
includes taxes & fees
18 Aug - 19 Aug
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 Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

8/10 Good
"The staff was very helpful, I enjoyed breakfast. I do recommend you guys adding water as an option for breakfast. The room was clean."
Miles 1-night trip
Posted less than an hour ago
Holiday Inn Express Springfield Downtown by IHG

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.