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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Windsor vacation rentals

Beach nearby

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (44 reviews)
"We had an awesome stay for Thanksgiving week!"
United States
Jamie S.
The price is AED 517
AED 1,138 total
includes taxes & fees
30 Jun - 1 Jul
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (51 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is AED 715
AED 1,385 total
includes taxes & fees
14 Jul - 15 Jul
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Terrace/patio

The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (18 reviews)
"Great location and pleasant area to walk to area restaurants and shops. Prompt and friendly communication with host who was very accommodating to our needs. We enjoyed our stay."
United States
Laurie R.
The price is AED 290
AED 1,146 total
includes taxes & fees
29 Jun - 30 Jun
The Blue Back Bungalow
Interior

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (40 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is AED 820
AED 1,530 total
includes taxes & fees
1 Jul - 2 Jul
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is AED 317
AED 438 total
includes taxes & fees
2 Jul - 3 Jul
Entire guest suite in South Windsor, Connecticut
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (14 reviews)
"We loved the home. "
United States
Karen D.
The price is AED 430
AED 1,208 total
includes taxes & fees
13 Jul - 14 Jul
The Serene Skyway Retreat
Smart TV, DVD player, books

Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!

Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"The apartment was perfect for my husband and me. It was clean and had everything we needed. The owners were very responsive when I had a question."
United States
Jenny T.
The price is AED 294
AED 1,199 total
includes taxes & fees
28 Jun - 29 Jun
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!
Property grounds

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 AED 441
AED 580 total
includes taxes & fees
29 Jun - 30 Jun
Humble Abode #2
Smart TV, offices

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is AED 325
AED 782 total
includes taxes & fees
5 Jul - 6 Jul
Crested One Place - with Free Parking, Heat & AC
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (23 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is AED 455
AED 819 total
includes taxes & fees
12 Jul - 13 Jul
Peaceful Meadow Retreat
Smart TV, offices, computer monitors

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 AED 372
AED 843 total
includes taxes & fees
5 Jul - 6 Jul
Central Chic Pad - with Free Parking, Heat & AC
Fridge, microwave, stovetop, coffee/tea maker

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (14 reviews)
"Amazing stay. Easy check-in/access and Karl was quick to answer any questions I had. The place was immaculate, clean and modern with all the amenities you’ll need. Very convenient and walkable to coffee shops, bars & restaurants. We’ll be back."
United States
Todd L.
The price is AED 314
AED 1,236 total
includes taxes & fees
29 Jun - 30 Jun
Charming Luxury 1BR Near Downtown. Dog Friendly!
Fridge, microwave, stovetop, coffee/tea maker

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
10.0 out of 10, Exceptional, (24 reviews)
"Perfect stay, second time, will be back, great for the show! "
United States
Kim G.
The price is AED 489
AED 636 total
includes taxes & fees
1 Jul - 2 Jul
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
The price is AED 314
AED 711 total
includes taxes & fees
28 Jun - 29 Jun
#2 *Beautiful 1 BR Apartment - Central CT*
TV

Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
The price is AED 350
AED 781 total
includes taxes & fees
29 Jun - 30 Jun
Tiny, Budget Friendly 1 Bedroom Central CT
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is AED 654
AED 1,306 total
includes taxes & fees
23 Jul - 24 Jul
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Interior

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 AED 533
AED 1,156 total
includes taxes & fees
30 Jun - 1 Jul
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is AED 774
AED 1,544 total
includes taxes & fees
27 Jul - 28 Jul
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Smart TV, offices

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 AED 414
AED 906 total
includes taxes & fees
29 Jun - 30 Jun
Premier League Pad - with Free Parking, Heat & AC
Interior

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, (13 reviews)
"Great place"
United States
Jason
The price is AED 463
AED 778 total
includes taxes & fees
30 Jun - 1 Jul
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
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

10/10 Excellent
"Clean, friendly staff, good breakfast!!!"
Christine 6-night trip
Posted 5 hours ago
Holiday Inn Express Southington 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 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 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.