Windsor Vacation Home Rentals from CA $266: Search Top Private Vacation Homes for Rent

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Our top choices for Windsor vacation homes

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

1. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

CA $296 total

includes taxes & fees

Sep 13 - Sep 14

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

2. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

CA $407 total

includes taxes & fees

Sep 13 - Sep 14

A wooden deck with a table and chairs, surrounded by a white railing.

3. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

CA $764 total

includes taxes & fees

Sep 11 - Sep 12

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Varun M.

CA $285 total

includes taxes & fees

Sep 10 - Sep 11

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

5. Cozy Home in Pownal VT

Pownal

Jess M.

CA $266 total

includes taxes & fees

Sep 13 - Sep 14

A hot tub with a string of lights above it, set against a dark night sky.

6. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

CA $574 total

includes taxes & fees

Sep 28 - Sep 29

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

CA $519 total

includes taxes & fees

Sep 10 - Sep 11

A hallway with wooden flooring, white walls, and a bed in the background.

8. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

CA $496 total

includes taxes & fees

Sep 17 - Sep 18

9. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Maura L.

CA $752 total

includes taxes & fees

Sep 11 - Sep 12

A spacious living room with a dining area, a kitchen, and a large window.

10. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

CA $325 total

includes taxes & fees

Sep 13 - Sep 14

A kitchen with white cabinets, a wooden dining table, and pendant lights.

11. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

CA $664 total

includes taxes & fees

Sep 17 - Sep 18

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

12. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveller

CA $590 total

includes taxes & fees

Sep 10 - Sep 11

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

13. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Diego G.

CA $783 total

includes taxes & fees

Sep 10 - Sep 11

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

14. The Greylock Cabin

Florida

Margaret M.

CA $687 total

includes taxes & fees

Oct 7 - Oct 8

A two-story house with a front porch, a small staircase leading to the door, and a pathway flanked by bushes and a lamp post.

15. North Getaway Cottage

Williamstown

Carole S.

CA $615 total

includes taxes & fees

Sep 17 - Sep 18

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

16. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

CA $826 total

includes taxes & fees

Sep 16 - Sep 17

A white two-story house with a porch, surrounded by trees and a hill.

17. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

CA $674 total

includes taxes & fees

Sep 10 - Sep 11

A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

18. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

CA $903 total

includes taxes & fees

Sep 10 - Sep 11

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

19. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

CA $1,584 total

includes taxes & fees

Sep 16 - Sep 17

An aerial view of a house surrounded by a forest with autumn foliage.

20. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jonathan

CA $738 total

includes taxes & fees

Sep 22 - Sep 23

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Top Windsor Hotel Reviews

Willows Motel Williamstown

10/10 Excellent

"Awesome staff plus pet-friendly."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews	213
Accommodation	286 Vacation Homes
Lowest Price	CA $266
Highest Price	CA $1,584

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor vacation homes

1. Private bed with En-suite bathroom Marigold Room

2. Real Estate: Therapy - Lake, Laundry, Love it

3. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!