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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windsor vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,180 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
$115 nightly
The price is $128
Nov 5 - Nov 6
Total with taxes and fees
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,712 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
$110 nightly
The price is $123
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

3. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
$306 nightly
The price is $342
Nov 2 - Nov 3
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A white building with a window, surrounded by trees and forest.

4. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
$412 nightly
The price is $460
Oct 8 - Oct 9
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

5. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.8 out of 10, Exceptional, (16 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
$252 nightly
The price is $281
Oct 8 - Oct 9
Total with taxes and fees
Penthouse Apartment on Park Street
A snow-covered outdoor area with a fire pit, tables, and chairs.

6. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
$256 nightly
The price is $286
Oct 13 - Oct 14
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A large building with a covered entrance and multiple windows, surrounded by snow-covered ground and parked cars.

7. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
8.6 out of 10, Excellent, (18 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
A two-story blue house with a porch, surrounded by a garden with orange flowers.

8. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
$132 nightly
The price is $148
Oct 8 - Oct 9
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

9. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

10. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
$240 nightly
The price is $268
Oct 8 - Oct 9
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

11. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
$248 nightly
The price is $279
Nov 4 - Nov 5
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

12. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$240 nightly
The price is $270
Nov 3 - Nov 4
Total with taxes and fees
New Studio In Town, By the Water
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

13. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
A Country Inn with a large, welcoming entrance and multiple parking spaces.

14. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
$256 nightly
The price is $286
Oct 13 - Oct 14
Total with taxes and fees
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Four people seated at a table with food and drinks, wearing winter sports helmets.

15. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
$231 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A stone bridge over a calm river with greenery on either side.

16. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$165 nightly
The price is $184
Nov 4 - Nov 5
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

17. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$209 nightly
The price is $233
Oct 28 - Oct 29
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

18. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
$208 nightly
The price is $222
Oct 12 - Oct 13
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

19. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
$275 nightly
The price is $309
Oct 19 - Oct 20
Total with taxes and fees
2-Bdr Apt In Town, By the Water
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

20. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$204 nightly
The price is $207
Oct 8 - Oct 9
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"
Frank 2-night trip
Posted 9 hours ago
Berkshire Mountain Lodge

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, there are vacation rentals close to well known attractions in Windsor, or you can select a more secluded option if you'd like a relaxing place to stay. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental near Windsor is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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 Pontoosuc Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Windsor. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.