Search Vacation Homes in Windsor

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 280 Vacation Homes in Windsor with updated reviews, rates, and availability.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just ā€œokā€ and hung up. Thankfully there was...
The price is SARĀ 446
SARĀ 582 total
includes taxes & fees
2 Jun - 3 Jun
Deluxe Queen Room with 2 Queen Beds

Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

Pristine Home In Becket Woods

9.8 out of 10, Exceptional, (15)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (32)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (73)
"Highly recommend this charming, historic place.Ā  Well appointed. Has everything you need for your stay.Ā  Cozy…yet plenty of space for everyone.Ā  Looks like it was just renovated.Ā  Took my daughter and two granddaughters for a ski weekend.Ā  Wouldn’t hesitate to come back here.Ā  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Becket Home w/ 3-Season Porch: Walk to Lake Access

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a clean, quiet spot for a nice weekend getaway. "
Becket Home w/ 3-Season Porch: Walk to Lake Access

Luxury Vacation Rental in the Berkshires!

10.0 out of 10, Exceptional, (13)
"Stayed here multiple times and will come back again. Great place to stay…"
Luxury Vacation Rental in the Berkshires!

Yacca House NEW Serene Retreat in Canaan

Yacca House NEW Serene Retreat in Canaan

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (20)
"The property was close to town and very cozy, clean & comfortable. Would highly recommend attention to the details was impressive."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Comfortable and relaxing spot. Really pretty lake. Fun stuff for paddling around the lake."
Berkshire Lake at the Pillow, and EV!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (7)
"Amazing view!!!They thought of everything even things we didn’t think we wanted, right down to little things like motion sensing lights in the bathrooms. I’m a chef and cooked for my friends and I was surprised they had everything I needed. We are looking forward to coming back for another stay."
Berkshires Lakefront Retreat

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

1840's Whaling Captain's Farm Estate, 6-10 guests

10.0 out of 10, Exceptional, (3)
"Such a beautiful home and property. We had a great time exploring during the day and spending time together at night. Sunsets over the pond are particularly lovely and the screened in porch and sitting around a fire in the chiminea outside are the perfect spots for a cocktail. We look forward to our next visit!"
1840's Whaling Captain's Farm Estate, 6-10 guests

Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

9.4 out of 10, Exceptional, (11)
"One of the best places we have stayed. Comfortable in every way. Great recommendations from the hosts."
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

Charming 3-bedroom farmhouse in Lenox

Charming 3-bedroom farmhouse in Lenox

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great place! Location was ideal, close to everything. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
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.
Save an average of 15% on thousands of hotels when you're signed in