Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Our top choices for Windsor holiday homes

New!Quaint & Convenient Hideaway: Great Location

9.8 out of 10, Exceptional, (12)
"Our family of 4 stayed there while visiting Hartford for our daughter’s college graduation. Great location great property and responsive host. Would def stay again!"
New!Quaint & Convenient Hideaway: Great Location

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

9.4 out of 10, Exceptional, (25)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (34)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is AU$518
includes taxes & fees
30 Sept - 1 Oct
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

9.0 out of 10, Wonderful, (10)
"Comfortable, clean and well maintained property. I definitely will book again. "
The price is AU$523
includes taxes & fees
8 Sept - 9 Sept
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

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

10.0 out of 10, Exceptional, (2)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (28)
"The house is very spacious, clean and comfortable. Will definitely book again!"
Prime West Hartford Center Location: Historic Gem

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

9.8 out of 10, Exceptional, (29)
"The place was clean and great for a weekend getaway."
The price is AU$483
includes taxes & fees
15 Sept - 16 Sept
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.4 out of 10, Exceptional, (6)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
The price is AU$955
includes taxes & fees
8 Sept - 9 Sept
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is AU$550
includes taxes & fees
7 Sept - 8 Sept
Big farmhouse in the foothills of the Berkshires

Newly Renovated 4 Bedroom House

10.0 out of 10, Exceptional, (2)
"The house was perfect for a weekend wedding trip. "
Newly Renovated 4 Bedroom House

Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (19)
"Great location, charming house. Well equipped and thoughtfully decorated."
Prime West Hartford Center: Timeless Charm

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 AU$499
includes taxes & fees
7 Sept - 8 Sept
Private Apartment in Berlin

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

9.2 out of 10, Wonderful, (9)
"Great stay"
The price is AU$523
includes taxes & fees
8 Sept - 9 Sept
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

#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

10.0 out of 10, Exceptional, (2)
"Well, the title says it all beautiful rooms, beautiful furniture, great kitchen, tons of room wonderful outdoor space took advantage of the fire pit didn’t get a chance to go on the lake as we were on another lake, but all their amenities just looked amazing. I could spend a week they are easy will be back saw a beautiful dear "
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

Blue Back Bungalow

2.0 star property
9.4 out of 10, Exceptional, (14)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AU$616
includes taxes & fees
8 Sept - 9 Sept
Blue Back Bungalow

Charming 3 bed/2 bath town home with gorgeous back yard

9.8 out of 10, Exceptional, (12)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
The price is AU$888
includes taxes & fees
10 Sept - 11 Sept
Charming 3 bed/2 bath town home with gorgeous back yard

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

10.0 out of 10, Exceptional, (59)
"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 AU$688
includes taxes & fees
7 Sept - 8 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

10.0 out of 10, Exceptional, (1)
"Clean and quiet location, great place for a relaxing stay."
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
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

Find out more about Windsor

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
Accommodation
215 Holiday Homes
Lowest Price
AU$483
Highest Price
AU$955