Weston, VT Vacation Homes from ￥29,933

Weston Vacation Homes
United States of America
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A red two-story building with a porch, labeled "The Vermont Country Store," featuring a sign for "The Orton Family Business."

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Our top choices for Weston vacation homes

A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

A bedroom with a wooden ceiling, a bed with a white and blue quilt, two bedside tables with lamps, and a chair.

A kitchen with wooden cabinets, a granite countertop, a microwave, three black stools, and a window with a forest view.

A cozy room with a leather sofa, a recliner, and a small table. Large windows offer a view of the outdoors.

1. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly

9.8 out of 10, Exceptional, (42 reviews)

9.8/10

Exceptional

(42 reviews)

"This house has great hang out space and plenty of space for a big family!"

Cheri V.

The price is ￥20,843

￥20,843

￥76,084 total

includes taxes & fees

Sep 13 - Sep 14

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

A multi-story building with a brick chimney, a snow-covered lawn, and a paved driveway.

A building with a sign that reads 'Long Trail House.'

A bedroom with a bed, a lamp, a television, and a window with a view of a snowy landscape.

2. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton

The price is ￥11,510

￥11,510

￥39,536 total

includes taxes & fees

Sep 15 - Sep 16

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

3. Secluded Spa Retreat | Hot Tub + Sauna | Okemo

Secluded Spa Retreat | Hot Tub + Sauna | Okemo

Ludlow

The price is ￥41,994

￥41,994

￥71,433 total

includes taxes & fees

Sep 18 - Sep 19

Secluded Spa Retreat | Hot Tub + Sauna | Okemo

4. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very nice stay. Owners were very gracious. House was clean & comfortable."

Lorraine C.

The price is ￥43,229

￥43,229

￥98,735 total

includes taxes & fees

Sep 13 - Sep 14

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

A wooden deck with a sofa and table, a house with white siding, and a clear sky.

A two-story blue house with a sloped roof, a front porch, and a deck.

A modern living room with a dark gray sectional sofa, a round wooden coffee table, and a patterned rug.

5. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow

10.0 out of 10, Exceptional, (18 reviews)

10/10

Exceptional

(18 reviews)

"This was a lovely, well-kept home in a great location to Okemo Mountain."

Nancy F.

The price is ￥41,407

￥41,407

￥92,325 total

includes taxes & fees

Sep 13 - Sep 14

New Ludlow Village Home with Stunning Okemo Mountain View

A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

A modern kitchen with wooden paneling, white cabinets, and a black countertop.

A spacious living room with a large sectional sofa, a stone fireplace, and a kitchen area visible through an open door.

A wooden interior with a kitchen area, bar stools, and a dining table.

6. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall

9.4 out of 10, Exceptional, (41 reviews)

9.4/10

Exceptional

(41 reviews)

"Our family had a wonderful vacation. The house and location were great. We will come back."

Victoria L.

The price is ￥30,469

￥30,469

￥102,364 total

includes taxes & fees

Sep 13 - Sep 14

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

A cozy living room with a fireplace, comfortable seating, and a television.

A wooden interior with a pool table, a sofa, and a dining area.

A bar area with wooden flooring, a trash can, and bar stools.

A wooden deck with a metal railing, a hanging bird feeder, and a view of a grassy yard with trees.

7. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Ludlow

The price is ￥30,909

￥30,909

￥65,937 total

includes taxes & fees

Sep 30 - Oct 1

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

A two-story house with a covered porch and a garage.

A modern kitchen with a central island, bar stools, pendant lighting, and a brick backsplash.

A stone pathway leading to a house with a well-maintained lawn and trees in the background.

8. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Mount Holly

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "

Chi L.

The price is ￥36,350

￥36,350

￥133,585 total

includes taxes & fees

Sep 13 - Sep 14

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

A two-story house with a front porch, a driveway, and autumn foliage.

9. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes

Chester Depot

9.4 out of 10, Exceptional, (22 reviews)

9.4/10

Exceptional

(22 reviews)

"Beautiful classic farmhouse in lovely neighbourhood."

Kimberly B.

The price is ￥32,268

￥32,268

￥65,190 total

includes taxes & fees

Sep 13 - Sep 14

Charming Chester Farmhouse near Near VT Slopes

A deck with outdoor furniture, a table, and a view of a forested hillside.

A kitchen with granite countertops, wooden cabinets, a refrigerator, a coffee maker, and a dining area with a table and chairs.

A living room with a wooden entertainment center, a flat-screen TV, a lamp, a potted plant, and a vintage suitcase.

A living room with a brown leather sectional sofa, a wooden coffee table, and a lamp.

10. Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!

Mount Holly

9.6 out of 10, Exceptional, (20 reviews)

9.6/10

Exceptional

(20 reviews)

"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."

Rachel L.

The price is ￥47,668

￥47,668

￥105,436 total

includes taxes & fees

Sep 17 - Sep 18

Modern Farm House…minutes to Okemo; 2 King beds!

A living room with a brick fireplace, a sofa, a chair, and a coffee table.

A house surrounded by autumn foliage with a mountain in the background.

A modern interior with a staircase, a dining area, and a living space with a fireplace.

A wooden tub with a wooden spoon resting on a grassy area near a pond, with a wooden structure in the background.

11. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"Clean, lots of room, easy access to Stratton, responsive host."

Mark H.

The price is ￥48,633

￥48,633

￥121,948 total

includes taxes & fees

Sep 21 - Sep 22

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

A residential property with a well-maintained lawn, a large flowering tree, and a house with a porch.

A living room with a pool table, a leather sofa, and a billiards cue rack.

A view through a window with a metal screen, a grassy area, a wooden fence, and a hill in the background.

12. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Mendon

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."

Aurore H.

The price is ￥14,240

￥14,240

￥36,226 total

includes taxes & fees

Sep 23 - Sep 24

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

A wooden dining table with chairs, a hanging light fixture, and large windows offering a view of the outdoors.

A loft-style room with a wooden dining table, a sofa, and a large window with a view of trees.

A kitchen with a Bosch dishwasher, wooden cabinets, a large window with a forest view, and a tiled backsplash.

13. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Jamaica

8.8 out of 10, Excellent, (8 reviews)

8.8/10

Excellent

(8 reviews)

"Beautiful home, we enjoyed our stay!"

Luke B.

The price is ￥64,072

￥64,072

￥94,576 total

includes taxes & fees

Sep 13 - Sep 14

A bedroom with a bed, curtains, a radiator, and a view of the outside.

A modern living room with a grey chair, a round coffee table, a grey sofa, and a white door.

A dining table set with plates, glasses, and a vase with a plant.

A modern kitchen with stainless steel appliances, a microwave, a toaster, and a sink.

14. Cozy Rutland Retreat

Cozy Rutland Retreat

Rutland

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"

Valerie

The price is ￥14,976

￥14,976

￥29,933 total

includes taxes & fees

Sep 20 - Sep 21

Cozy Rutland Retreat

A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

A spacious kitchen with a large island, wooden cabinets, and a dining area with a piano.

A rustic kitchen with wooden cabinets, a bar area, and a fireplace.

A dining area with a wooden table, four chairs, a central vase with flowers, and a view of greenery outside.

15. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home

Manchester

The price is ￥48,724

￥48,724

￥122,406 total

includes taxes & fees

Sep 13 - Sep 14

1812 House, 2 Stays, 1 home

A two-story white house with a front porch, a door with a wreath, and a chimney.

A dining area with a wooden table, six chairs, a patterned rug, and a wall-mounted light fixture.

A porch with two black chairs and a small table, a yellow patterned rug, and a vase of flowers.

A kitchen with dark wooden cabinets, stainless steel appliances, a window with blinds, and a wooden floor.

16. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Manchester

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "

Marissa H.

The price is ￥58,359

￥58,359

￥115,318 total

includes taxes & fees

Sep 18 - Sep 19

Cozy farmhouse in Manchester - short drive to multiple ski mountains!

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

A dining area with a table and chairs, a large arched window, and a view of a grassy landscape.

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

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

17. 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, (4 reviews)

10/10

Exceptional

(4 reviews)

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

pauline

The price is ￥83,232

￥83,232

￥155,470 total

includes taxes & fees

Sep 18 - Sep 19

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

A red building with a gabled roof, surrounded by a well-maintained grassy field and dense trees.

A living room with a television, floral-patterned sofas, a green cabinet, and framed artwork on the walls.

An outdoor seating area with a stone table and red chairs, surrounded by rocks and plants.

A red house with a gravel driveway and lush greenery.

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

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

Plymouth

The price is ￥27,534

￥27,534

￥88,479 total

includes taxes & fees

Sep 16 - Sep 17

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

A wooden cabin with a green door, a small porch, and a set of stairs leading to the entrance.

A cozy attic bedroom with wooden walls, a ceiling fan, two beds with plaid bedding, a small table with chairs, and a window with a view of greenery.

A cabin with a loft bed, a small table with a folder, a chair, and a view of a deck and mountains.

A cozy room with a wooden ceiling, a round table with chairs, a small cabinet, and a view of a green landscape through a door.

19. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells

Wells

The price is ￥28,341

￥28,341

￥36,389 total

includes taxes & fees

Sep 23 - Sep 24

Peaceful 1-bedroom bungalow with AC in charming Wells

A modern living room with a dark gray sectional sofa, a white armchair, a wooden coffee table, and a spiral staircase.

A hot tub on a wooden deck with a grill and potted plants.

A two-story house with a stone facade, a large garage, and a gravel driveway.

A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

20. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill

Killington

The price is ￥23,159

￥23,159

￥153,018 total

includes taxes & fees

Sep 14 - Sep 15

Slopeside Estate Guesthouse: Hot tub, AC, Grill

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 Weston Hotel Reviews

The Mountain Inn at Killington

8/10 Good

"The restaurant was not open even though I checked on line before reserving my room. Everything else was great!"

Ginger 1-night trip

Posted less than an hour ago

The Mountain Inn at Killington

The Manchester View

10/10 Excellent

"This was a spectacular place to stay. Staff was very fruendly and helpful. They got the hot tub going for us and started a fire in case we wanted to enjoy sitting by it. Very quaint continental breakfast with attention to detail. Would definitelt stay here again."

cynthia 1-night trip

Posted 4 hours ago

The Manchester View

Bromley View Inn

10/10 Excellent

"Clean and quiet little inn with a beautiful view"

Cristion 1-night trip

Posted 4 hours ago

Bromley View Inn

Aspen At Manchester

8/10 Good

"No interaction with the staff. They were invisible. The water stream in the shower was weak, but everything else was very good."

Izhar 2-night trip

Posted 6 hours ago

Aspen At Manchester

Hampton Inn Rutland

10/10 Excellent

"Clean!!"

Shelly 1-night trip

Posted 7 hours ago

Hampton Inn Rutland

Comfort Inn Rutland - Killington

8/10 Good

"The room was clean & the staff very helpful. We were pleasantly surprised by the substantial breakfast which came with our booking & loved the pool/hot tub. It was older but very clean!"

Susan 1-night trip

Posted 2 days ago

Comfort Inn Rutland - Killington

Pointe at Castle Hill Resort

10/10 Excellent

"Wonderful experience. Beautiful, clean room and friendly/helpful front desk"

Darlene 1-night trip

Posted 2 days ago

Pointe at Castle Hill Resort

Brittany Motel

10/10 Excellent

"Very friendly staff. The room was cozy and quiet."

David 1-night trip

Posted 2 days ago

Brittany Motel

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good

"The room was very nice and the staff was very helpful. This is a motel. I didn’t realize that when I made my reservation. We enjoyed out stay."

Marilyn 2-night trip

Posted 6 days ago

The Palmer House Resort, an Ascend Collection Hotel

Find out more about Weston

Weston Vacation Homes information

Number of reviews	140
Accommodation	831 Vacation Homes
Lowest Price	￥29,933
Highest Price	￥155,470

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Book Vacation Homes in Weston on Expedia.com

Search Vacation Homes in Weston

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Weston vacation homes

1. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

2. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

3. Secluded Spa Retreat | Hot Tub + Sauna | Okemo

4. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

5. New Ludlow Village Home with Stunning Okemo Mountain View

6. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

7. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

8. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

9. Charming Chester Farmhouse near Near VT Slopes

10. Modern Farm House…minutes to Okemo; 2 King beds!

11. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

12. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

13. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

14. Cozy Rutland Retreat

15. 1812 House, 2 Stays, 1 home

16. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

17. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

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

19. Peaceful 1-bedroom bungalow with AC in charming Wells

20. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Find vacation rentals that suit your style

Top Weston Hotel Reviews

The Mountain Inn at Killington

Find out more about Weston

Weston Vacation Homes information

Explore a world of travel with Expedia