Cavendish Vacation Homes

A coastal landscape with a sandy beach, dense forest, and a clear blue sea under a partly cloudy sky.

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Our top choices for Cavendish holiday homes

A bunk bed room with a small table and a door labeled 'Ranger House'.

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

Ludlow

HK$3,452 total

includes taxes & fees

30 Sept - 1 Oct

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

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

Ludlow

HK$2,983 total

includes taxes & fees

30 Sept - 1 Oct

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

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

HK$7,424 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Mt Holly

Cheri V.

HK$3,751 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Plymouth

HK$4,241 total

includes taxes & fees

29 Sept - 30 Sept

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

6. New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow

Nancy F.

HK$4,416 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Mount Holly

Chi L.

HK$6,199 total

includes taxes & fees

29 Sept - 30 Sept

8. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

HK$3,128 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Mendon

Aurore H.

HK$1,797 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Killington

HK$7,287 total

includes taxes & fees

5 Oct - 6 Oct

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

11. Luxury Condo Tucked in the Heart of Killington

Killington

HK$2,072 total

includes taxes & fees

29 Sept - 30 Sept

A spacious living area with a fireplace, a dining area, and a kitchen.

12. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Ludlow

"My family and I stayed at this property last weekend and it was amazing!!! We were the first to rent as this is a brand new construction home. Everything inside is brand new from the bedding, furniture and amazing cookware. This house has a few great features that make it top notch: 1: Every bedroom has an en-suite bathroom, so we all had our own space and privacy. The bedrooms were big and beds were so comfortable. The master bedroom has this huge shower and tub that was so nicely designed. 2:...

Michael

HK$16,788 total

includes taxes & fees

29 Sept - 30 Sept

A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

13. Killington Retreat | Deck-Fire Pit-Mountain Views!

Clarendon

Ahmad H.

HK$3,329 total

includes taxes & fees

24 Oct - 25 Oct

A large house with a fire pit and outdoor seating.

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

Bridgewater

Susan S.

HK$4,296 total

includes taxes & fees

26 Oct - 27 Oct

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

Andover

Lorraine C.

HK$4,735 total

includes taxes & fees

29 Sept - 30 Sept

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

16. Cozy Rutland Retreat

Rutland

Valerie

HK$1,470 total

includes taxes & fees

27 Oct - 28 Oct

A hot tub surrounded by snow, with lounge chairs and string lights.

17. Fall Getaway Near Killington with Hot Tub

Bridgewater

HK$5,028 total

includes taxes & fees

30 Sept - 1 Oct

A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

18. CozyDen - AC, Bike to Mountain, Porch!

Killington

Berni H.

HK$2,057 total

includes taxes & fees

1 Oct - 2 Oct

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

19. Lakefront Family Fun Retreat

Newport

Ann R.

HK$3,319 total

includes taxes & fees

21 Oct - 22 Oct

A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

20. large ski ranch hot tub close to killington pets ok

Mendon

Callison A.

HK$3,522 total

includes taxes & fees

5 Oct - 6 Oct

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Top Cavendish Hotel Reviews

Fireside Inn & Suites West Lebanon

10/10 Excellent

"Great place and great staff"

Mountain Meadows Lodge

10/10 Excellent

"What an incredible find! We booked this property on a whim on our way back from Boston through Vermont, hoping to get a really mountain/wilderness feel and this checked every box and then some. More of a b&b vibe in the best of ways. Shout out to the property manager Mike who functioned as tour guide, cook, and purveyor of incredible hospitality. We loved the hot tub, sauna, dock, kayaks and trails. Not to mention the delicious and plentiful breakfast, one of the best “hotel breakfast” I’ve ever had. Rooms were clean, spacious and extremely comfortable bed. While we visited in the fall I can see why people would choose this for skiing in the winter as it’s fully equipt for this and all seasons. We were traveling from Canada and will absolutely make a point of coming back here on another trip! We did not want to leave and our following night in Stowe was a letdown in comparison!"

Woodstock Inn & Resort

10/10 Excellent

"Our 2nd floor room with balcony was beautiful, large, clean, and with excellent amenities, also looking over the waterfront. The bed was very comfortable. We enjoyed breakfast each morning very much. Our server is friendly and helpful. We were able to get close-in parking. Desk staff were also friendly. We visited Kelleyway Gardens and spoke with Clement. She is a delightful young lady who offered good information about the area. This was our second stay and we will visit again."

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