Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Windsor vacation rentals

Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,235 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is ￥16,064
￥19,638 total
includes taxes & fees
Feb 12 - Feb 13
Vacation Village in the Berkshires
Exterior

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (8 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ￥26,004
￥29,046 total
includes taxes & fees
Mar 8 - Mar 9
Huttopia Berkshires
Daily to-go breakfast for a fee

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ￥29,202
￥32,619 total
includes taxes & fees
Mar 8 - Mar 9
Jiminy Peak Mountain Resort
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (28 reviews)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is ￥10,429
￥22,065 total
includes taxes & fees
Feb 12 - Feb 13
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior

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

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is ￥14,215
￥27,786 total
includes taxes & fees
Mar 5 - Mar 6
2 Twin beds on 1st floor with En-suite bathroom.
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥30,284
￥85,541 total
includes taxes & fees
Feb 21 - Feb 22
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (1 review)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ￥15,945
￥29,281 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Home in Pownal VT
TV

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ￥28,391
￥50,418 total
includes taxes & fees
Mar 5 - Mar 6
Florida Mountain Log Cabin
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is ￥20,086
￥44,667 total
includes taxes & fees
Feb 22 - Feb 23
Downtown | Waterfront | Walk to Shops
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (11 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is ￥18,541
￥42,411 total
includes taxes & fees
Mar 8 - Mar 9
2-Bdr Apt In Town, By the Water
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ￥24,753
￥60,958 total
includes taxes & fees
Feb 23 - Feb 24
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
TV, fireplace, books

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Charlemont
10.0 out of 10, Exceptional, (1 review)
The price is ￥34,610
￥103,381 total
includes taxes & fees
Feb 24 - Feb 25
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Property grounds

Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is ￥108,157
￥136,171 total
includes taxes & fees
Feb 23 - Feb 24
Cozy Valley View Post & Beam Villa!
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ￥24,722
￥65,239 total
includes taxes & fees
Feb 12 - Feb 13
Riverbend Berkshire East Basecamp - 3 bedrooms available
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is ￥18,541
￥41,693 total
includes taxes & fees
Feb 12 - Feb 13
New Studio In Town, By the Water
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ￥16,687
￥52,088 total
includes taxes & fees
Feb 12 - Feb 13
Near Tanglewood: Historic Summer Retreat
Beach

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is ￥19,839
￥39,105 total
includes taxes & fees
Feb 22 - Feb 23
Berkshires Apartment at the Stephentown Hotel
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
The price is ￥32,853
￥57,678 total
includes taxes & fees
Mar 5 - Mar 6
The Greylock Cabin
Property grounds

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥36,928
￥80,254 total
includes taxes & fees
Mar 4 - Mar 5
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is ￥42,490
￥93,101 total
includes taxes & fees
Mar 10 - Mar 11
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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
"Perfect location, big rooms, nice staff. "
Dana 2-night trip
Posted 14 hours ago
Berkshire Mountain Lodge

Find out more about Windsor

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Look no further and take a look at our great range of rental properties in Windsor!

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental near Windsor offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Mount Greylock 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.