Holiday Rentals 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

This weekend
Next weekend

Holiday Rentals in Windsor

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is €141
includes taxes & fees
1 Apr - 2 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is €136
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (240)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is €217
includes taxes & fees
1 Apr - 2 Apr
Berkshire Village Carriage House - Super Private!!

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is €300
includes taxes & fees
1 Apr - 2 Apr
Near Tanglewood: Historic Summer Retreat

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature

Peace and quiet on the lake

9.6 out of 10, Exceptional, (211)
"This property was in an incredible location with a nice cozy feel. It was perfect for my family of 6. I highly recommend this place!"
Peace and quiet on the lake

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is €981
includes taxes & fees
4 Apr - 5 Apr
Hancock Village Inn at Jiminy Peak

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (212)
"The house was small, cozy and even had a small stream that ran through the backyard and under the deck. It had everything we needed. A bigger TV in the living room but definitely be a big upgrade but that isn't the end of the world. Would stay here again. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Comfortable Berkshires retreat on mtn resort, SISO

"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is €460
includes taxes & fees
2 Apr - 3 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (43)
"Did a ski weekend with a bunch of friends, the house was perfect, the character of the place and unique styling of each room was super fun, the hot tub was actually HOT, which was impressive for how cold it was outside. The house used to be an old bed and breakfast and it lends itself beautifully to being a VRBO for a large group. We had a wonderful time and would definitely come back and rent again! "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Bear Creek Cabin

9.8 out of 10, Exceptional, (27)
"Perfect place to stay while skiing Berkshire East! Clean, spacious, and beautiful surroundings!"
The price is €566
includes taxes & fees
1 Apr - 2 Apr
Bear Creek Cabin

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (31)
"The pictures were absolutely spot on! The space was incredibly quiet and cozy, with a warm and inviting atmosphere—even in zero-degree weather. The hot tub was fantastic, and the heated bathroom floors were a luxurious touch. The WiFi worked flawlessly throughout the property. The chef’s kitchen was spacious and well-equipped, making it perfect for cooking. Plus, the rental is conveniently close to town, and the breathtaking mountain views made the stay even more special. Highly recommend!"
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

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

9.2 out of 10, Wonderful, (10)
"Simply loved the property! Enjoyed relaxing on the porch and sitting by the waterfall. Location was central to other sites we wanted to visit, too! We lost power overnight in the storm but made it work. Owner kept in contact with us and even started working on alternatives for us! Ran to get batteries for the lantern the house had and ice for the cooler to save our food! A few more candles and flashlights would have been great, but otherwise, a gem! Thku for your hospitality!"
The price is €293
includes taxes & fees
1 Apr - 2 Apr
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Windsor you may be interested in

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (535)
"Enjoyed having an excellent meal and bar was very convenient. "
The price is €100
includes taxes & fees
13 Apr - 14 Apr
Life House Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1136)
"We highly recommend it!! My husband go there often for work and we usually stayed there. Very nice place!! "
The price is €91
includes taxes & fees
7 Apr - 8 Apr
The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is €141
includes taxes & fees
1 Apr - 2 Apr
Vacation Village in the Berkshires
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.

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

What are some of the best holiday rentals that Windsor has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Windsor is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Wahconah Falls State Park. Mount Greylock State Reservation Visitor Center and Swift River are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.