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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Cuttingsville vacation homes

Interior
Beautiful home offering privacy on 7 acres with private pond

Beautiful home offering privacy on 7 acres with private pond

Beautiful home offering privacy on 7 acres with private pond
West Windsor
10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
United States
Roy S.
The price is AED 747
AED 1,787 total
includes taxes & fees
16 Dec - 17 Dec
Beautiful home offering privacy on 7 acres with private pond
Interior
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated
Cavendish
9.6 out of 10, Exceptional, (4)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
The price is AED 582
AED 1,092 total
includes taxes & fees
16 Dec - 17 Dec
The Dorothy-10 minutes from Okemo- freshly renovated
Fridge, microwave, oven, stovetop
Mountain Stay | Skiing | Hiking | Sleeps 8

Mountain Stay | Skiing | Hiking | Sleeps 8

Mountain Stay | Skiing | Hiking | Sleeps 8
Bridgewater
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 AED 779
AED 2,086 total
includes taxes & fees
16 Dec - 17 Dec
Mountain Stay | Skiing | Hiking | Sleeps 8
Interior
Charming Cavendish Guesthouse

Charming Cavendish Guesthouse

Charming Cavendish Guesthouse
Cavendish
9.8 out of 10, Exceptional, (7)
"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."
United States
deborah m.
Charming Cavendish Guesthouse
House, 2 Bedrooms | Exterior
Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home
3.0 star property
North Sherburne
The price is AED 597
AED 2,078 total
includes taxes & fees
16 Dec - 17 Dec
Bob's Sled Lodge 2 Bedroom Home
Terrace/patio
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
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 AED 716
AED 2,073 total
includes taxes & fees
16 Dec - 17 Dec
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Killington
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 AED 472
AED 1,214 total
includes taxes & fees
17 Dec - 18 Dec
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Property grounds
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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
The price is AED 848
AED 1,676 total
includes taxes & fees
16 Dec - 17 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Indoor pool, a heated pool
Bearmont- Pool, HotTub, Fireplace

Bearmont- Pool, HotTub, Fireplace

Bearmont- Pool, HotTub, Fireplace
The Woods
10.0 out of 10, Exceptional, (6)
"Great location and a great place. Felt right at home"
United States
Tyler B.
The price is AED 508
AED 1,844 total
includes taxes & fees
16 Dec - 17 Dec
Bearmont- Pool, HotTub, Fireplace
Fridge, microwave, oven, stovetop
Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
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 AED 688
AED 1,520 total
includes taxes & fees
14 Jan - 15 January 2026
Luxury Condo Tucked in the Heart of Killington
Outdoor spa tub
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
2.0 star property
Killington
10.0 out of 10, Exceptional, (2)
"This was a perfect property for our quick vacation. The house is very well equipped and you have everything you need for a relaxing fun stay in Killington. The hot tub was great, and the house is in a very convenient location while fairly private at the same time. We really enjoyed our stay and would definitely recommend staying here."
United States
Linda D.
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
Property grounds
Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.

Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.

Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.
Killington
10.0 out of 10, Exceptional, (2)
"A very comfortable stay for a family of four. Close to everything, clean, well stocked for breakfast making, and just enough room for everyone. We really enjoyed the fireplace after a day of skiing.Not sure why the heat setting turned to low 60s every night, but our blankets were warm."
United States
Maria K.
The price is AED 509
AED 1,617 total
includes taxes & fees
16 Dec - 17 Dec
Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.
Golf
TheGrizz! Shuttle on/off!

TheGrizz! Shuttle on/off!

TheGrizz! Shuttle on/off!
Killington
10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
United States
Angela S.
TheGrizz! Shuttle on/off!
Dining
4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
2.0 star property
North Sherburne
10.0 out of 10, Exceptional, (22)
"Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway."
United States
Darko G.
The price is AED 727
AED 2,475 total
includes taxes & fees
16 Dec - 17 Dec
4BR Killington Home Perfect for Families, Pet-Friendly
House, 3 Bedrooms | Interior
Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home

Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home

Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home
3.0 star property
Killington
Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home
Spa
large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
2.0 star property
Mendon
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 AED 618
AED 1,708 total
includes taxes & fees
16 Dec - 17 Dec
large ski ranch hot tub close to killington pets ok
Exterior
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
2.0 star property
Killington
The price is AED 513
AED 1,414 total
includes taxes & fees
16 Dec - 17 Dec
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Exterior
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
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 AED 859
AED 1,693 total
includes taxes & fees
16 Dec - 17 Dec
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Fridge, microwave, oven, stovetop
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Outdoor spa tub
Whitetail Chalet at Killington: 4BR/2BA

Whitetail Chalet at Killington: 4BR/2BA

Whitetail Chalet at Killington: 4BR/2BA
2.0 star property
Killington
10.0 out of 10, Exceptional, (2)
"A beautiful property which is very well equipped and really well kept. Great communication and wish we could have stayed longer. "
United Kingdom
John P.
Whitetail Chalet at Killington: 4BR/2BA
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 Cuttingsville Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Yea"
Robert Miller 1-night trip
Posted 3 days ago
Pointe at Castle Hill Resort