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Cuttingsville Vacation Rentals

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Our top choices for Cuttingsville vacation rentals

1. 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 CA $130
CA $326 total
includes taxes & fees
Sep 23 - Sep 24
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

2. 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, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is CA $189
CA $688 total
includes taxes & fees
Sep 24 - Sep 25
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

3. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $72
CA $320 total
includes taxes & fees
Sep 23 - Sep 24
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is CA $78
CA $416 total
includes taxes & fees
Sep 30 - Oct 1
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

5. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"I enjoy the location "
United States
troy
The price is CA $109
CA $326 total
includes taxes & fees
Sep 23 - Sep 24
Mountain Green

6. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
The price is CA $103
CA $402 total
includes taxes & fees
Sep 23 - Sep 24
Welcoming condo near the slopes with free WiFi and full kitchen

7. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is CA $139
CA $270 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Rutland Retreat

8. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (22 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is CA $202
CA $664 total
includes taxes & fees
Sep 23 - Sep 24
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

9. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is CA $147
CA $376 total
includes taxes & fees
Sep 23 - Sep 24
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

10. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
8.0 out of 10, Very good, (1 review)
The price is CA $91
CA $333 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

11. Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful location with Mountain views. Property owners were wonderful hosts."
United States
Jane
The price is CA $157
CA $208 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful 1-bedroom cabin with AC in wonderful Wells

12. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is CA $176
CA $331 total
includes taxes & fees
Sep 23 - Sep 24
Bridgewater Living - Ben&Jerry Suite

13. 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, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is CA $131
CA $522 total
includes taxes & fees
Sep 23 - Sep 24
Resort condo with mountain views, full kitchen, and free WiFi

14. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is CA $113
CA $366 total
includes taxes & fees
Sep 23 - Sep 24
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

15. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is CA $307
CA $1,181 total
includes taxes & fees
Sep 23 - Sep 24
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

16. Killington resort: Walk to Mountain, Bike, Pool

Killington resort: Walk to Mountain, Bike, Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is CA $163
CA $491 total
includes taxes & fees
Sep 23 - Sep 24
Killington resort: Walk to Mountain, Bike, Pool

17. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was great"
United States
Nathan H.
The price is CA $108
CA $355 total
includes taxes & fees
Sep 23 - Sep 24
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

18. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is CA $160
CA $502 total
includes taxes & fees
Sep 23 - Sep 24
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

19. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
The price is CA $103
CA $349 total
includes taxes & fees
Sep 23 - Sep 24
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

20. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
The price is CA $154
CA $445 total
includes taxes & fees
Sep 24 - Sep 25
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
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

Find out more about Cuttingsville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cuttingsville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Cuttingsville?

Yes, we have vacation rentals close to top attractions in Cuttingsville, or you can select a secluded option if you're looking for relaxation.

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

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Cuttingsville 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.

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 Killington Peak. In the larger area, you’ll find Shrewsbury Free Library and Calvin Coolidge Historic Site.

What’s a vacation rental in Cuttingsville like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Cuttingsville. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for small groups.