Windsor Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windsor Vacation Homes

Grammy's Lake House w/ Private Waterfront Access
Enjoy breathtaking views of the lake and surrounding residential area from the comfort of your room.

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access
3-bedroom house in perfect Springfield with WiFi, AC
Relax in this stylish living room with a large flat-screen TV, comfortable sofa, and patterned rug.

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
3-bedroom house in perfect Springfield with WiFi, AC
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is CA $275
CA $500 total
includes taxes & fees
Aug 11 - Aug 12
Big farmhouse in the foothills of the Berkshires
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is CA $398
CA $671 total
includes taxes & fees
Aug 18 - Aug 19
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Lake Congamond Cozy Stylish Comfortable House
Enjoy a serene lakeside retreat with a boat dock and tranquil views.

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (4)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
Enjoy cooking in this well-lit kitchen with a refrigerator, microwave, and double oven.

New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

2.0 star property
10.0 out of 10, Exceptional, (6)
"Everything about our stay at this property was great. Communication, check-in, cleanliness, etc. The location is directly across the street from Wesleyan University which made my son's visit all the better. I will definately stay here again."
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
Mountaintop Horse Farm with Heated Pool
Relax by the pool surrounded by lush greenery and a traditional house in the background.

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (31)
"This a the most unique place! A very clean and comfortable apartment above a barn with beautiful horses and more. Wonderful hosts too. We hope to be back! "
Mountaintop Horse Farm with Heated Pool
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Relax by the fire pit in a serene forest setting, surrounded by comfortable seating.

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The price is CA $374
CA $689 total
includes taxes & fees
Aug 15 - Aug 16
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Modern Luxury, The Perfect Getaway Awaits
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a dining area.

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (2)
"Super clear, spacious, house looks just like the photos. Very easy communication with the host. Thank you!"
The price is CA $402
CA $730 total
includes taxes & fees
Aug 11 - Aug 12
Modern Luxury, The Perfect Getaway Awaits
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Cozy living room with a comfortable sofa, coffee table, and fireplace.

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (23)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Enjoy a well-equipped kitchen with a central sink, stainless steel faucet, and a window offering a view of the surrounding greenery.

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (27)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Fully equipped kitchen with gas stove, oven, microwave, and coffee maker.

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

9.0 out of 10, Wonderful, (2)
"Mini family vacation. The property was pleasant and convenient to the Museums and Zoo.This is not specific to this stay, but I wish the fees would be available prior to the booking/ payment process. We had to stop the booking of a different property for this trip when the hidden fees more than doubled the cost of the rental."
The price is CA $285
CA $496 total
includes taxes & fees
Aug 11 - Aug 12
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
The price is CA $182
CA $569 total
includes taxes & fees
Aug 14 - Aug 15
Private Apartment in Berlin
Modern & Cozy Cape | 4 Bedroom House | Central Location
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and dishwasher.

Modern & Cozy Cape | 4 Bedroom House | Central Location

10.0 out of 10, Exceptional, (5)
"We had a great stay in this house. It provided everything we needed for a comfortable and enjoyable visit. All the rooms were clean, tidy, and well-maintained, creating a welcoming environment. The host was exceptionally helpful and quick to respond to any questions or needs we had, which made our experience even better. We highly recommend this house for anyone looking for a hassle-free and pleasant stay."
The price is CA $177
CA $404 total
includes taxes & fees
Aug 11 - Aug 12
Modern & Cozy Cape | 4 Bedroom House | Central Location
Prime West Hartford Center: Timeless Charm
Relax on the outdoor deck with a sofa set and armchairs, surrounded by lush greenery and a central fire pit.

Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (17)
"Very comfortable and clean accommodations in walking distance to stores and many restaurant options. Highly recommend for anyone needing lodging in West Hartford. "
Prime West Hartford Center: Timeless Charm
Private Yard & Covered Deck: Vintage Windsor Home
Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and refrigerator, complemented by ample natural light and a ceiling fan.

Private Yard & Covered Deck: Vintage Windsor Home

9.0 out of 10, Wonderful, (8)
"Great rentsl. The location was convenient to the airport. The house was clean and well kept. "
Private Yard & Covered Deck: Vintage Windsor Home
#26 Beautifully Renovated 2 BR Home
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, dishwasher, and coffee maker.

#26 Beautifully Renovated 2 BR Home

10.0 out of 10, Exceptional, (2)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
#26 Beautifully Renovated 2 BR Home
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Fridge, microwave, oven, stovetop

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
PICON COZY
Enjoy cooking in this fully equipped kitchen with a microwave, coffee maker, and refrigerator.

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is CA $98
CA $228 total
includes taxes & fees
Aug 22 - Aug 23
PICON COZY
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Madeline at the front desk and all staff are very welcoming and professional. Hot breakfast is good and accomodations are clean and comfortable. GPS guided me into adjacent parking lot not affiliated with the hotel."
Efrain 1-night trip
Posted 15 hours ago
The Capitol Hotel