Windsor County Vacation Rentals from ￥9,992: Search Short-Term Rentals

A historic courthouse with a prominent clock tower and a brick facade.

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A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'

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Our top choices for Windsor County vacation rentals

A two-story wooden house with a covered porch and two Adirondack chairs.

1. Fat Sheep Farm & Cabins

Windsor

Brenda

￥28,315 total

includes taxes & fees

Nov 30 - Dec 1

A room with a wicker chair and a matching ottoman, large windows with a view of a garden, and string lights on the ceiling.

2. Addie's Place: A Quiet and Quirky Guesthouse

Hartford

Victor R.

￥39,358 total

includes taxes & fees

Nov 15 - Nov 16

A large house with a fire pit and outdoor seating.

3. Bridgewater Living - Ben&Jerry Suite

Bridgewater

Sylvia F.

￥32,917 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with stainless steel appliances, a wooden dining table set with plates, and a hanging light fixture.

4. Cozy Village Condo-Okemo Shuttle

Ludlow

walter s.

￥39,930 total

includes taxes & fees

Nov 14 - Nov 15

A wooden deck with a covered seating area, a grill, and string lights.

5. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Sharon

Kat V.

￥42,986 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with a curved edge, surrounded by lounge chairs and a stone wall.

6. Condo a short walk to the Sachem trail with seasonal pool and tennis

Ludlow

￥47,298 total

includes taxes & fees

Nov 16 - Nov 17

A fireplace with a mantel displaying a framed picture, a clock, and a vase with flowers.

7. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

￥41,351 total

includes taxes & fees

Nov 18 - Nov 19

A building with multiple floors, a red curved structure, and a flower bed with purple flowers.

8. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Clock Tower Base Area

Danna K.

￥43,166 total

includes taxes & fees

Nov 16 - Nov 17

A wooden cabin interior with a staircase, a sofa, and a table.

9. Adventure Cabin Hot Tub Sauna Trails Game Area

Cavendish

Katherine B.

￥65,410 total

includes taxes & fees

Nov 17 - Nov 18

A house with a pond in a lush green landscape.

10. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Ludlow

￥70,240 total

includes taxes & fees

Nov 16 - Nov 17

A golf course with a winding path, trees, and a distant mountain range.

11. Compact downtown studio condo with kitchenette near the Okemo slopes

Ludlow

Frank R.

￥38,675 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a porch, a staircase, and a front door.

12. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Ludlow

Zach S.

￥44,942 total

includes taxes & fees

Nov 16 - Nov 17

A golf course with a winding path, trees, and a hilly landscape.

13. First-floor downtown studio near dining and gear shops, under a mile to Okemo

Ludlow

Brian

￥50,410 total

includes taxes & fees

Nov 16 - Nov 17

A red house with a gravel driveway and lush greenery.

14. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

Plymouth

￥99,811 total

includes taxes & fees

Nov 15 - Nov 16

A covered porch with wicker furniture, a table, and chairs.

15. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Cavendish

Mark G.

￥88,039 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with Adirondack chairs and a table, overlooking a mountainous landscape.

16. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

￥90,777 total

includes taxes & fees

Nov 16 - Nov 17

17. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

￥90,777 total

includes taxes & fees

Nov 16 - Nov 17

A golf course with a clubhouse, surrounded by lush greenery and hills.

18. Village Fireplace Shuttle Boot Warmers

Ludlow

Justin P.

￥67,522 total

includes taxes & fees

Nov 30 - Dec 1

A wooden deck with two chairs and a small table, overlooking a green landscape.

19. Game Room, Fire Pit & Views! Spacious Ludlow Home

Ludlow

￥126,389 total

includes taxes & fees

Nov 15 - Nov 16

20. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Bridgewater

Lisa G.

￥82,117 total

includes taxes & fees

Nov 14 - Nov 15

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Find vacation rentals that suit your style

Top Windsor County Hotel Reviews

A large, snow-covered house with multiple windows and a well-lit porch.

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

Snowed Inn

Killington

10/10 Excellent

Tammy

A white single-story house with a black roof, a front porch, and a small garden with pink flowers.

The Lyme Inn

Lyme

10/10 Excellent

gayle

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A large, white two-story house with a stone wall and yellow flowers in the foreground.

The Inn at Ormsby Hill

Manchester Center

10/10 Excellent

The Inn at Ormsby Hill is a magnificent B&B in historic Manchester Vermont. We were in Vermont for a ski week vacation. We ended our trip staying at this Inn and skiing at Stratton Ski Area. When we arrived, the Innkeeper Maryanne greeted us then suggested we move our room to one more centrally located. Our room was beautiful with a 4 post king bed, gas fireplace and plush bathrobes. The daily breakfast was superb! The dining area was full of antiques, many from the Pullman Corporation. Edward...

Anonymous traveler

An outdoor patio with a table and chairs, surrounded by a grassy area and trees.

Shoreham Inn

Shoreham

10/10 Excellent

Nice inn located in a 200 year old house. Rooms with comfortable beds, no tv, but they do have WiFi. Food is very good and the couple that owns and runs the inn is very friendly and accommodating. Some quirks like squeaky floors and no locks on the doors just add to the charm. Nice fireplace and outdoor deck. Coffee is excellent too. Very nice place to stay you have something going on in the area, or if you want a relaxing low key vacation in picturesque Vermont or nearby upstate NY.

Ron

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

Mountain Meadows Lodge

Killington

10/10 Excellent

Timothy

A cozy room with a wooden staircase, a fireplace, a sofa, and a patterned rug.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

A wooden bench by a river with a forest backdrop.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A modern living room with a fireplace, sofas, and a dining area.

Six South St Hotel

Hanover

10/10 Excellent

Lynn

Find out more about Windsor County

Vacation Apartments in Windsor County

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Vacation Rentals in Windsor County

Change your mind

Treat yourself

Be picky

Top cities in Windsor County

Woodstock

Check prices for these dates

Our top choices for Windsor County vacation rentals

1. Fat Sheep Farm & Cabins

2. Addie's Place: A Quiet and Quirky Guesthouse

3. Bridgewater Living - Ben&Jerry Suite

4. Cozy Village Condo-Okemo Shuttle

5. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

6. Condo a short walk to the Sachem trail with seasonal pool and tennis

7. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

8. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

9. Adventure Cabin Hot Tub Sauna Trails Game Area

10. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

11. Compact downtown studio condo with kitchenette near the Okemo slopes

12. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

13. First-floor downtown studio near dining and gear shops, under a mile to Okemo

14. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

15. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

16. Ski Home/Arcade Mountain Views Near Killington/Woodstock

17. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

18. Village Fireplace Shuttle Boot Warmers

19. Game Room, Fire Pit & Views! Spacious Ludlow Home

20. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Find vacation rentals that suit your style

Top Windsor County Hotel Reviews

The Inn at Manchester

10/10 Excellent

Find out more about Windsor County

Vacation Apartments in Windsor County