Windsor County Holiday Rentals: Short-Term Accommodations for Rent

Holiday Rentals in Windsor County
United States of America
Holiday Rentals
Expedia.com.hk

Windsor County Hotels Windsor County Car Hire Windsor County Holidays

A river flowing through a forest with autumn foliage.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Our top choices for Windsor County holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

A kitchen with wooden cabinets, a white stove, a microwave, and pendant lights.

A living room with a spiral staircase, a sofa set, a coffee table, and a painting on the wall.

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

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3.0 star property

Windsor

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Woman who runs the place is great, such a nice little cabin beautiful views! "

Jessica

The price is HK$882

HK$882

HK$1,389 total

includes taxes & fees

3 Nov - 4 Nov

Fat Sheep Farm & Cabins

A sunroom with wicker furniture, large windows, and string lights.

A house with a red door, a window with white trim, a wooden porch with potted plants, and a wooden bench.

A bedroom with a sofa, a bedside table with a lamp, a bed with floral bedding, and a window with curtains.

A house with a red door, a porch with steps, and a wooden fence in the background.

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

Addie's Place: A Quiet and Quirky Guesthouse

Hartford

9.6 out of 10, Exceptional, (19 reviews)

9.6/10

Exceptional

(19 reviews)

"Nice cottage setting in a quiet neighborhood, my dogs loved it!"

Victor R.

The price is HK$1,019

HK$1,019

HK$1,824 total

includes taxes & fees

28 Oct - 29 Oct

Addie's Place: A Quiet and Quirky Guesthouse

A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

An indoor swimming pool with multiple lanes, wooden beams, and a tiled floor.

A brick building with arched windows and a sign reading 'Simon Pearce Glass.'

A sign for Quechee Falls Park with a waterfall in the background.

3. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Hartford

10.0 out of 10, Exceptional, (179 reviews)

10/10

Exceptional

(179 reviews)

"Clean, well maintained property. Perfect decor for a quaint Vermont town."

Joann

The price is HK$1,389

HK$1,389

HK$3,272 total

includes taxes & fees

25 Oct - 26 Oct

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

A large house with a fire pit and outdoor seating.

A kitchen area with a coffee maker, a kettle, and a microwave. There are framed pictures on the wall, including one of Ben & Jerry's.

A hotel room with a bed, a desk, a refrigerator, and a microwave.

4. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite

Bridgewater

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"

Sylvia F.

The price is HK$784

HK$784

HK$1,615 total

includes taxes & fees

15 Nov - 16 Nov

Bridgewater Living - Ben&Jerry Suite

A wooden cabin interior with a staircase leading to a loft, a kitchen area, and large windows offering views of the surrounding forest.

A wooden cabin with a red exterior, surrounded by snow-covered ground and trees.

A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

A wooden cabin bedroom with a bed, two windows, a robe hanging, and a wall-mounted lamp.

5. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Cavendish

10.0 out of 10, Exceptional, (29 reviews)

10/10

Exceptional

(29 reviews)

"We had a great stay. The hot tub was perfect after a long day of skiing."

Michael L.

The price is HK$1,560

HK$1,560

HK$3,182 total

includes taxes & fees

18 Nov - 19 Nov

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

A spacious living area with a large sofa, a coffee table, and a TV. There are multiple windows offering a view of the outdoors.

A compact kitchen with wooden cabinetry, a central island with bar stools, a microwave, and a refrigerator.

A house with a bright pink door, a balcony with a railing, and two potted plants on either side of the door.

6. 180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck

Hartford

9.0 out of 10, Wonderful, (8 reviews)

9.0/10

Wonderful

(8 reviews)

"Plenty of room beautiful view"

Anthony A.

The price is HK$2,207

HK$2,207

HK$4,212 total

includes taxes & fees

25 Oct - 26 Oct

180-degree panoramic views of Vermont's mountains from the living room and Deck

A person standing on a sandy beach by a river with trees in the background.

A room with wooden walls, a ceiling fan, a window with curtains, a small table with a chair, and a sign on the wall.

A cabin with a deck, surrounded by dense forest.

A room with two wooden beds, a dresser, and a chair.

7. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms

West Windsor

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."

Alvin

The price is HK$2,313

HK$2,313

HK$4,279 total

includes taxes & fees

25 Oct - 26 Oct

Cabin on the hill Ascutney Vt - 4 bedrooms

A picnic table and a fire pit by a lake with a forest in the background.

A cozy living room with a brown leather sofa, a wooden coffee table, and a bookshelf. A staircase leads to an upper level.

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

A blue building with a kayak, a tree, and a shed.

8. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

3.0 star property

Ludlow

The price is HK$1,458

HK$1,458

HK$2,658 total

includes taxes & fees

25 Oct - 26 Oct

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

A stone pathway leading to a rustic outdoor seating area with a fire pit, surrounded by a forested landscape.

A golf course with multiple holes, water hazards, and a forested backdrop.

Two brown wicker chairs with checkered pillows, a small table with a vase and a book, and a white ottoman.

A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

9. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Hartford

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Wonderful and well appointed abode - super cozy!"

Nina S.

The price is HK$2,328

HK$2,328

HK$6,934 total

includes taxes & fees

11 Nov - 12 Nov

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

A compact kitchen with a refrigerator, stove, microwave, and sink.

A rural setting with a red house, a wooden barn, and a snowy landscape.

A spacious loft with high ceilings, large windows, and a cozy seating area.

A spacious living area with a high ceiling, a dining area, and a kitchen with wooden cabinets.

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

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

Plymouth

The price is HK$1,399

HK$1,399

HK$4,444 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern living room with a dark sofa, white curtains, a large plant, and a fur rug.

A modern kitchen with a central island, wooden bar stools, and a fireplace.

A hotel room with a bed, desk, chair, and large windows.

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

Pet Friendly | Game Room | Minutes to Woodstock and Killington

Bridgewater

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"

Lisa G.

The price is HK$1,569

HK$1,569

HK$4,095 total

includes taxes & fees

25 Oct - 26 Oct

Pet Friendly | Game Room | Minutes to Woodstock and Killington

A spacious living room with a stone fireplace, wooden furniture, and large windows.

A kitchen with white cabinets, stainless steel appliances, and a granite countertop.

A modern, multi-story wooden cabin with a sloped roof, a covered porch, and a gravel driveway.

A spacious living area with a large sectional sofa, a dining table, and a kitchen in the background.

12. Hawk Mountain renovated condo with central A/C off Scenic Route 100

Hawk Mountain renovated condo with central A/C off Scenic Route 100

Plymouth

9.8 out of 10, Exceptional, (24 reviews)

9.8/10

Exceptional

(24 reviews)

"convenient to okemo"

marcus l.

Hawk Mountain renovated condo with central A/C off Scenic Route 100

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A compact kitchen with white cabinets, a dishwasher, and a countertop with various appliances.

A living room with a flat-screen TV, a sofa, a coffee table, and a lamp.

A two-story house with a porch, a white picket fence, and a tree in front.

13. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

9.8 out of 10, Exceptional, (114 reviews)

9.8/10

Exceptional

(114 reviews)

"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."

Tina l.

The price is HK$1,740

HK$1,740

HK$3,958 total

includes taxes & fees

18 Nov - 19 Nov

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

A modern living room with a black leather sofa, wooden flooring, and exposed wooden beams on the ceiling.

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

A compact kitchen with a sink, microwave, and stainless steel refrigerator.

14. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ludlow

9.8 out of 10, Exceptional, (109 reviews)

9.8/10

Exceptional

(109 reviews)

"Great location right in town and close to Okemo."

Justin P.

The price is HK$1,513

HK$1,513

HK$3,376 total

includes taxes & fees

22 Nov - 23 Nov

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

A two-story house with a deck, surrounded by dense forest.

A dining area with a wooden table and chairs, a large arched window, and a view of trees outside.

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a white table and grey chairs.

A red cabin with a wooden deck and a large window, surrounded by snow-covered ground and trees.

15. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Clean, spacous house, good location and great scenes of the mountains."

pauline

The price is HK$4,225

HK$4,225

HK$7,839 total

includes taxes & fees

24 Oct - 25 Oct

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

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

A living room with a fireplace, a dining area, and a kitchen visible through an archway.

A modern living room with a sofa, coffee table, and dining table.

16. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Cavendish

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Such a beautiful place and we loved the area. It was our first trip to Vermont. "

Mark G.

The price is HK$1,255

HK$1,255

HK$4,066 total

includes taxes & fees

4 Nov - 5 Nov

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

A multi-story building with balconies, a grassy area, and trees with autumn foliage.

A modern kitchen with white cabinets, a central island, and wooden chairs.

A modern living room with a sofa, chairs, a coffee table, a TV, and a kitchen area with bar stools.

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

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

Clock Tower Base Area

9.2 out of 10, Wonderful, (30 reviews)

9.2/10

Wonderful

(30 reviews)

"Great property, clean and close to the slope"

tiliger01

The price is HK$403

HK$403

HK$1,819 total

includes taxes & fees

26 Oct - 27 Oct

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

A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

A living room with a brown sofa, a wooden coffee table, and a patterned rug.

Two blue Adirondack chairs in a forest with a fire pit between them.

A kitchen with wooden cabinets, a black stove, a refrigerator, and a window with a view of trees.

18. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Bridgewater

8.8 out of 10, Excellent, (3 reviews)

8.8/10

Excellent

(3 reviews)

"Great place for a ski weekend"

Kathryn F.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

A wooden deck with a table, chairs, a bottle of wine, and a glass.

A dining area with a wooden table, chairs, and a hanging light fixture. Large windows offer a view of trees and hills.

A rustic wooden cabin surrounded by dense forest.

19. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"

Gerald S.

The price is HK$1,653

HK$1,653

HK$3,836 total

includes taxes & fees

4 Nov - 5 Nov

Gnome Home Mountain Ski Chalet w/Sauna Killington

A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

A gym with various exercise machines, a treadmill, and a mirror on the wall.

A living room with a fireplace, a sofa, a table, and a cabinet.

A dining area with a white table and chairs, a chandelier, and a kitchen in the background.

20. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Cavendish

10.0 out of 10, Exceptional, (25 reviews)

10/10

Exceptional

(25 reviews)

"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "

Ania H.

The price is HK$2,351

HK$2,351

HK$4,266 total

includes taxes & fees

1 Nov - 2 Nov

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

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.

View all properties