A sign with a coat of arms and the word 'CAVENDISH' against a blue sky.

Cavendish Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Cavendish vacation rentals

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

1. Adventure Cabin Hot Tub Sauna Trails Game Area

Cavendish

Katherine B.

AED 1,483 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Cavendish

Mark G.

AED 1,827 total

includes taxes & fees

11 Nov - 12 Nov

A cabin interior with a wooden staircase, a kitchen with modern appliances, and large windows offering a forest view.

3. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

Cavendish

Joe C.

AED 1,442 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Cavendish

Ania H.

AED 1,884 total

includes taxes & fees

14 Nov - 15 Nov

A cabin interior with a wooden staircase, kitchen area, and large windows offering a forest view.

5. Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes

Cavendish

Kristen A.

AED 1,442 total

includes taxes & fees

11 Nov - 12 Nov

A residential property with a swimming pool, a covered patio, and a detached garage.

6. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

Cavendish

AED 2,174 total

includes taxes & fees

11 Nov - 12 Nov

A snow-covered street with houses, a church steeple, and mountains in the background.

7. Cozy Village Condo-Okemo Shuttle

Ludlow

walter s.

AED 942 total

includes taxes & fees

11 Nov - 12 Nov

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

8. Fat Sheep Farm & Cabins

Windsor

Brenda

AED 651 total

includes taxes & fees

17 Nov - 18 Nov

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

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

Clock Tower Base Area

tiliger01

AED 837 total

includes taxes & fees

13 Nov - 14 Nov

A view of a grassy area with a ski lift and a building in the background.

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

Clock Tower Base Area

Danna K.

AED 947 total

includes taxes & fees

15 Nov - 16 Nov

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.

AED 864 total

includes taxes & fees

13 Nov - 14 Nov

A bedroom with a bed, a window with curtains, a ceiling fan, and a kitchenette.

12. Downtown studio with kitchenette, shuttle stop right across the street

Ludlow

Mikhail R.

AED 889 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Ludlow

Zach S.

AED 1,004 total

includes taxes & fees

13 Nov - 14 Nov

A large house with a fire pit and outdoor seating.

14. Bridgewater Living - Ben&Jerry Suite

Bridgewater

Sylvia F.

AED 720 total

includes taxes & fees

11 Nov - 12 Nov

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

15. Village Fireplace Shuttle Boot Warmers

Ludlow

Justin P.

AED 1,557 total

includes taxes & fees

30 Nov - 1 Dec

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

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

Ludlow

Tina l.

AED 1,754 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Chester

pauline

AED 3,501 total

includes taxes & fees

11 Nov - 12 Nov

18. Bridgewater Living - Ski VT Suite

Bridgewater

AED 716 total

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a fireplace, a television, and a ceiling fan.

19. Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst

Ludlow

Carey S.

AED 1,853 total

includes taxes & fees

22 Nov - 23 Nov

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

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

Mt Holly

Cheri V.

AED 1,720 total

includes taxes & fees

11 Nov - 12 Nov

View all properties

Find vacation rentals that suit your style

Top Cavendish Hotel Reviews

A rustic dining area with wooden beams, tables, chairs, and a fireplace.

The Inn at Weathersfield

Perkinsville

10/10 Excellent

Robert

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

Pointe at Castle Hill Resort

Cavendish

10/10 Excellent

This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...

Marion

A large stone building with a steep roof, surrounded by dense forest and hills.

Castle Hill Resort And Spa

Cavendish

10/10 Excellent

STAFF I want to start by pointing out that the staff at the hotel were above and beyond PHENOMENAL, and I mean ALL THE STAFF. I spent the weekend up there and got stuck with some car problems in a blizzard and dealt with everybody on the staff there. They were some of the nicest people I have ever dealt with in the hospitality industry. When I say all the staff, I mean all the staff! DAY 1. The plow guy helped me get my car out of a spot when my snow chain broke and I couldn’t move. DAY 2...

Steven

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 stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

10/10 Excellent

Jamie

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

10/10 Excellent

Volodymyr N.

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

Best Western Springfield Hotel

Springfield

10/10 Excellent

JULIA

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

On The River Inn

West Woodstock

10/10 Excellent

Ayleen

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

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 two-story house with a front porch, a central entrance, and a garden with various plants and flowers.

Kedron Valley Inn

South Woodstock

10/10 Excellent

Anonymous traveler

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

Woodstock Inn & Resort

Woodstock

10/10 Excellent

Anonymous traveler

A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

Echo Lake Inn

Plymouth

10/10 Excellent

Deb

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

Fat Sheep Farm & Cabins

Windsor

10/10 Excellent

Brenda

Snowed Inn

Killington

10/10 Excellent

Tammy

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

Frequently Asked Questions

Can I find vacation rentals in Cavendish?

Yes, there are vacation rentals close to popular attractions in Cavendish, or you can choose a more secluded option if you want a relaxing place to stay. The ski slopes and spas are just a few reasons why tourists like Cavendish. Allow lots of time to check out the mountain landscape and restaurants during your visit.

What's the top vacation rental in Cavendish?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental outside of Cavendish is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Cavendish?

Choose from 27 Expedia vacation rentals in Cavendish for a memorable vacation.

What’s there to see and do in Cavendish?

Explore the area and family-friendly sights such as Maple Lanes, or get out into nature at a spot like Lake Rescue. Phineas Gage Memorial and Fox Run Golf Course are a couple of places you'll find in the larger area.

What’s a vacation rental in Cavendish like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Cavendish. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips.

Cavendish Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cavendish vacation rentals

1. Adventure Cabin Hot Tub Sauna Trails Game Area

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

3. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

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

5. Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes

6. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

7. Cozy Village Condo-Okemo Shuttle

8. Fat Sheep Farm & Cabins

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

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

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

12. Downtown studio with kitchenette, shuttle stop right across the street

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

14. Bridgewater Living - Ben&Jerry Suite

15. Village Fireplace Shuttle Boot Warmers

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

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

18. Bridgewater Living - Ski VT Suite

19. Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst

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

Find vacation rentals that suit your style

Top Cavendish Hotel Reviews

The Inn at Weathersfield

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Cavendish?

What's the top vacation rental in Cavendish?

How many vacation rentals are there in Cavendish?

What’s there to see and do in Cavendish?

What’s a vacation rental in Cavendish like?