Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Savoy

4.98 out of 5 average rating, 184 reviews

The Camp - 20 Minutes to Berkshire East!

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

Aug 25 – Sep 1

R2,160 ZAR per night
Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 257 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen bed & desk. Apt. Is 2 min's to Rt. 2 Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes.

Jul 23 – 30

R1,985 ZAR per night
Guest favorite

Cabin in Cummington

4.98 out of 5 average rating, 159 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Sep 22 – 29

R1,274 ZAR per night

Popular amenities for Windsor vacation rentals

Other great vacation rentals in Windsor

Guest favorite

Apartment in Shelburne Falls

4.96 out of 5 average rating, 286 reviews

Annies’ Place by The Bridge of Flowers ~

Jan 4 – 11

R1,942 ZAR per night
Guest favorite

Apartment in Pittsfield

4.83 out of 5 average rating, 153 reviews

HawksNest: quiet 2BR apt, heart of the Berkshires

Apr 10 – 17

R1,303 ZAR per night
Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 155 reviews

Hilltown Studio

Dec 1 – 8

R2,334 ZAR per night
Guest favorite

Apartment in North Adams

4.9 out of 5 average rating, 100 reviews

Cozy 1 bedroom 1/2 mile to MassMoca

Jul 15 – 22

R1,876 ZAR per night
Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 248 reviews

Wildlife Lakeside Cottage

Feb 4 – 11

R5,174 ZAR per night
Guest favorite

Home in Dalton

4.99 out of 5 average rating, 120 reviews

Cleveland House - renovated Berkshires' gem.

Dec 30 – Jan 6

R9,114 ZAR per night
Guest favorite

Guest suite in Greenfield

4.94 out of 5 average rating, 143 reviews

Pristine Oasis with Private Bath

Nov 10 – 17

R1,337 ZAR per night
Guest favorite

Apartment in Northampton

4.96 out of 5 average rating, 272 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Apr 30 – May 7

R1,976 ZAR per night
Guest favorite

Loft in Shelburne Falls

4.95 out of 5 average rating, 261 reviews

The Railroad House

Aug 30 – Sep 6

R1,743 ZAR per night
Guest favorite

Apartment in Shelburne Falls

4.98 out of 5 average rating, 480 reviews

In town, newly renovated studio with private deck

Feb 12 – 19

R2,709 ZAR per night
Guest favorite

Apartment in Adams

4.88 out of 5 average rating, 57 reviews

Mountain Living, 1-bedroom unit, outdoor hot-tub

Jun 10 – 17

R1,834 ZAR per night
Guest favorite

Home in Adams

4.91 out of 5 average rating, 64 reviews

Mountain View Hideaway

Feb 11 – 18

R2,242 ZAR per night

Destinations to explore