Cuttingsville Holiday Rentals

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Our top choices for Cuttingsville holiday rentals

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (37 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is AU$439
includes taxes & fees
26 May - 27 May
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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 AU$842
includes taxes & fees
21 May - 22 May
Terrific 3-bedroom cottage with AC in charming Cavendish

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 AU$754
includes taxes & fees
21 May - 22 May
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

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 AU$382
includes taxes & fees
28 May - 29 May
Mountain Green

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)
"Great location, "
United States
Bryan R J.
The price is AU$406
includes taxes & fees
21 May - 22 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

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 AU$582
includes taxes & fees
26 May - 27 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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 AU$1,146
includes taxes & fees
21 May - 22 May
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

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)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AU$464
includes taxes & fees
21 May - 22 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is AU$263
includes taxes & fees
27 May - 28 May
Cozy Rutland Retreat

Your perfect pet friendly, summer retreat w/ serene brook, hot tub and fire pit.

Your perfect pet friendly, summer retreat w/ serene brook, hot tub and fire pit.
Peru
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is AU$966
includes taxes & fees
21 May - 22 May
Your perfect pet friendly, summer retreat w/ serene brook, hot tub and fire pit.

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 AU$827
includes taxes & fees
21 May - 22 May
New Ludlow Village Home with Stunning Okemo Mountain View

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 AU$933
includes taxes & fees
24 May - 25 May
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

Quaint lakefront home with great views & full kitchen

Quaint lakefront home with great views & full kitchen
Poultney
8.2 out of 10, Very good, (25 reviews)
"A nice place"
United States
Robert B.
The price is AU$577
includes taxes & fees
26 May - 27 May
Quaint lakefront home with great views & full kitchen

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 AU$671
includes taxes & fees
21 May - 22 May
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AU$464
includes taxes & fees
21 May - 22 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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 AU$537
includes taxes & fees
26 May - 27 May
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"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 AU$783
includes taxes & fees
26 May - 27 May
Large Killington Area Home | Sleeps 7 | Game Room

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is AU$484
includes taxes & fees
26 May - 27 May
Resort condo with mountain views, full kitchen, and free WiFi

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 AU$367
includes taxes & fees
21 May - 22 May
Okemo | Studio Condo + Loft | Near Slopes + Pool

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AU$1,070
includes taxes & fees
21 May - 22 May
Breakaway House by Killington Vacation Rentals
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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Find out more about Cuttingsville

Everything you need to know about Cuttingsville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttingsville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cuttingsville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cuttingsville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cuttingsville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cuttingsville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttingsville holiday rentals we have selected for you start as low as AU$382 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cuttingsville rentals

At Expedia, we put the best Cuttingsville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cuttingsville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cuttingsville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cuttingsville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.