Cuttingsville Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Cuttingsville holiday rentals

Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (24 reviews)
"I enjoy the location "
United States
troy
The price is HK$1,376
HK$1,846 total
includes taxes & fees
13 May - 14 May
Mountain Green
Dining

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, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is HK$2,101
HK$4,684 total
includes taxes & fees
4 May - 5 May
New Ludlow Village Home with Stunning Okemo Mountain View
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (17 reviews)
"It was an amazing experience! "
United States
Gruha
The price is HK$1,234
HK$2,268 total
includes taxes & fees
3 May - 4 May
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
The price is HK$979
HK$3,266 total
includes taxes & fees
2 May - 3 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Microwave, oven, stovetop, dishwasher

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is HK$3,525
HK$6,825 total
includes taxes & fees
4 May - 5 May
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Indoor pool

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is HK$3,525
HK$6,506 total
includes taxes & fees
7 May - 8 May
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is HK$1,072
HK$2,247 total
includes taxes & fees
3 May - 4 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Smart TV, fireplace, video games, books

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, (41 reviews)
"Very easy check in and out and clean home. Streets nearby can be hard to travel without 4 wheel drive. "
United States
Andrew O.
The price is HK$1,058
HK$3,860 total
includes taxes & fees
2 May - 3 May
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Outdoor pool, a heated pool

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

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great communication without host. The property is clean, well stocked and well maintained. Would definitely stay again! Thanks for letting us share your space."
United States
Steve G.
The price is HK$2,350
HK$4,211 total
includes taxes & fees
2 May - 3 May
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Interior

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"This condo is a true ski-in, ski-out experience! Literally walked out the back door and skied to the lift. (A/B lifts) The kitchen was well appointed, the bed comfortable, and was perfectly set up for a ski vacation. The entire space had a comfortable, rustic vibe. Would definitely stay here again when returning to Okemo."
United States
Patricia D.
The price is HK$1,175
HK$3,018 total
includes taxes & fees
3 May - 4 May
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
Interior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is HK$1,762
HK$4,702 total
includes taxes & fees
4 May - 5 May
Terrific 3-bedroom cottage with AC in charming Cavendish
Interior

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, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is HK$881
HK$2,385 total
includes taxes & fees
3 May - 4 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Interior

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is HK$415
HK$2,299 total
includes taxes & fees
2 May - 3 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Interior

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Killington
10.0 out of 10, Exceptional, (83 reviews)
"Family have fun"
United States
Yanyi
The price is HK$3,133
HK$4,045 total
includes taxes & fees
3 May - 4 May
Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Outdoor dining

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very good, (13 reviews)
"Great layout for our family of five!"
United States
Jennifer P.
The price is HK$2,813
HK$5,657 total
includes taxes & fees
2 May - 3 May
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
Private kitchen

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)
"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 HK$776
HK$1,895 total
includes taxes & fees
3 May - 4 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Smart TV, fireplace, DVD player, video library

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill
chittenden
10.0 out of 10, Exceptional, (30 reviews)
"We had a great family gathering at this property while enjoying a family wedding! Perfect space to enjoy time together."
United States
Kristen W.
The price is HK$4,582
HK$7,870 total
includes taxes & fees
2 May - 3 May
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$588
HK$2,032 total
includes taxes & fees
2 May - 3 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Outdoor dining

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is HK$1,617
HK$2,060 total
includes taxes & fees
4 May - 5 May
Okemo | Studio Condo + Loft | Near Slopes + Pool
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
"Beautiful "
Ronald 2-night trip
Posted 5 hours ago
Pointe at Castle Hill Resort

Find out more about Cuttingsville

Search for holiday rentals in Cuttingsville on Expedia! You can easily find your home rentals, villas, holiday apartments in Cuttingsville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cuttingsville!

Frequently asked questions

Can I find a holiday rental in Cuttingsville?

Yes, there are holiday rentals close to the most popular sights in Cuttingsville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cuttingsville has to offer?

Okemo Mountain Lodging by Vail Resorts: This holiday home rental outside of Cuttingsville is in the mountains and offers an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

What’s there to see and do in Cuttingsville?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Buttermilk Falls. In the wider area, you’ll find Shrewsbury Free Library and Killington Peak.

What’s a holiday rental in Cuttingsville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cuttingsville. Holiday rentals offer amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.