Holiday Homes in Cavendish

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Cavendish holiday homes

Fridge, microwave, oven, stovetop
Lake Front Family Friendly Escape

Holiday Home in Newport

Lake Front Family Friendly Escape
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is €314
includes taxes & fees
12 Jan - 13 Jan 2026
Lake Front Family Friendly Escape
Interior
Whimsical Room & Private Bathroom in Historic Inn

Holiday Home in Chester Depot

Whimsical Room & Private Bathroom in Historic Inn
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is €176
includes taxes & fees
4 Jan - 5 Jan 2026
Whimsical Room & Private Bathroom in Historic Inn
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is €291
includes taxes & fees
7 Jan - 8 Jan 2026
Chester Farmhouse Ski Retreat near Slopes
Terrace/patio
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Holiday Home in Bridgewater

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is €497
includes taxes & fees
13 Jan - 14 Jan 2026
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Interior
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Holiday Home in Mendon

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
9.8 out of 10, Exceptional, (6)
"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."
United States
Aurore H.
The price is €245
includes taxes & fees
4 Jan - 5 Jan 2026
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Holiday Home in Pomfret

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
10.0 out of 10, Exceptional, (4)
"Enjoyed the cleanliness and the convenience of being close to Woodstock, and not too far from Stowe."
United States
Dee Dee H.
The price is €387
includes taxes & fees
29 Dec - 30 Dec
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Holiday Home in Londonderry

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2.0 star property
8.0 out of 10, Very good, (1)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is €424
includes taxes & fees
5 Jan - 6 Jan 2026
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Fridge, microwave, oven, stovetop
Luxury Condo Tucked in the Heart of Killington

Holiday Home in Killington

Luxury Condo Tucked in the Heart of Killington
8.0 out of 10, Very good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is €344
includes taxes & fees
13 Jan - 14 Jan 2026
Luxury Condo Tucked in the Heart of Killington
Interior
large ski ranch hot tub close to killington pets ok

Holiday Home in Mendon

large ski ranch hot tub close to killington pets ok
2.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing stay! Gorgeous house, clean, perfect location. The host was super responsive and made the check in check out process so easy.Highly reccomend and can’t wait to stay again next year. "
United States
Nicole H.
The price is €647
includes taxes & fees
11 Jan - 12 Jan 2026
large ski ranch hot tub close to killington pets ok
Interior
180-degree panoramic views of Vermont's mountains from the living room and Deck

Holiday Home in Hartford

180-degree panoramic views of Vermont's mountains from the living room and Deck
8.0 out of 10, Very good, (2)
"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "
United States
Mary Anne C.
The price is €613
includes taxes & fees
25 Jan - 26 Jan 2026
180-degree panoramic views of Vermont's mountains from the living room and Deck
House, 6 Bedrooms | Private kitchen
Breakaway House by Killington Vacation Rentals

Holiday Home in Killington

Breakaway House by Killington Vacation Rentals
2.0 star property
Breakaway House by Killington Vacation Rentals
Smart TV, fireplace
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Holiday Home in Bridgewater Corners

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
10.0 out of 10, Exceptional, (4)
"Very clean, cozy, & had exactly what we needed for the last leg of our vacation. Bed was comfy, & nice to have the hot tub, we appreciated that after all the driving. We had just stayed at a vrbo that was not clean, so it was a great contrast! Thanks Russ & family for sharing your cute little cottage with us! Mark & Sherry"
United States
Sherry M.
The price is €398
includes taxes & fees
19 Jan - 20 Jan 2026
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Fridge, microwave, oven, stovetop
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Holiday Home in Mt Holly

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is €574
includes taxes & fees
7 Jan - 8 Jan 2026
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Property grounds
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Holiday Home in Ludlow

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
9.8 out of 10, Exceptional, (104)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is €444
includes taxes & fees
13 Jan - 14 Jan 2026
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Holiday Home in Killington

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
10.0 out of 10, Exceptional, (1)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
The price is €490
includes taxes & fees
4 Jan - 5 Jan 2026
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Fridge, microwave, oven, stovetop
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Holiday Home in Rutland

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
10.0 out of 10, Exceptional, (1)
The price is €374
includes taxes & fees
6 Jan - 7 Jan 2026
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Fridge, microwave, oven, stovetop
Killington Area Home | Sleeps 8 | Game Room

Holiday Home in Bridgewater

Killington Area Home | Sleeps 8 | Game Room
9.6 out of 10, Exceptional, (7)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is €698
includes taxes & fees
4 Jan - 5 Jan 2026
Killington Area Home | Sleeps 8 | Game Room
Exterior
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Holiday Home in Ludlow

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is €444
includes taxes & fees
13 Jan - 14 Jan 2026
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Fridge, microwave, oven, stovetop
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Holiday Home in Jamaica

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
9.0 out of 10, Wonderful, (6)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
The price is €684
includes taxes & fees
13 Jan - 14 Jan 2026
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Exterior
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Holiday Home in Killington

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
2.0 star property
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cavendish Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Staff are exceptionally friendly and helpful "
Brandon 1-night trip
Posted 3 days ago
Pointe at Castle Hill Resort

Find out more about Cavendish

Cavendish Holiday Homes information

Number of reviews
246
Accommodation
868 Holiday Homes
Lowest Price
€176
Highest Price
€698

Explore a world of travel with Expedia