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Cuttingsville Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Cuttingsville vacation rentals

A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

1. 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.
$407 nightly
The price is $456
Nov 8 - Nov 9
Total with taxes and fees
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

2. 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
9.4 out of 10, Exceptional, (8 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.
$186 nightly
The price is $210
Nov 8 - Nov 9
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A living room with a sofa, armchair, coffee table, TV, fireplace, and artwork on the wall.

3. Newly renovated cozy ski retreat with view of Killington slopes

Newly renovated cozy ski retreat with view of Killington slopes
Killington
9.6 out of 10, Exceptional, (53 reviews)
"This condo was very warm and cozy and few steps away from the Grand Resort hotel where my conference was taking place. The condo complex included workout room and hot tub/pool. Wayne was very communicative and a gracious host. I highly recommend this reasonable stay in a beautiful resort village of Killington."
United States
Suzanne
$334 nightly
The price is $378
Nov 8 - Nov 9
Total with taxes and fees
Newly renovated cozy ski retreat with view of Killington slopes
A two-story house with a covered porch and a garage.

4. 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.
$692 nightly
The price is $766
Nov 9 - Nov 10
Total with taxes and fees
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A hallway with a wooden wall, a white door, and a wooden staircase.

5. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (8 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
$349 nightly
The price is $351
Nov 8 - Nov 9
Total with taxes and fees
4BR Home | Walk Downtown Rutland + Trails
A modern cabin with a stone chimney, wooden balconies, and a hot tub.

6. Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.
Killington
9.6 out of 10, Exceptional, (73 reviews)
"This is a great house. Super comfortable and the location is amazing. Real ski in ski out. "
United States
Zvi
$1,039 nightly
The price is $1,174
Nov 8 - Nov 9
Total with taxes and fees
Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.
A spacious living area with a dining table, chairs, a sofa, and a large window.

7. SunBear-Ski on Ski off, Pool, HotTub, Game Room!

SunBear-Ski on Ski off, Pool, HotTub, Game Room!
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Very accommodating and helpful hosts"
United States
Sean W.
$481 nightly
The price is $544
Nov 10 - Nov 11
Total with taxes and fees
SunBear-Ski on Ski off, Pool, HotTub, Game Room!
A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

8. Village Fireplace Shuttle Boot Warmers

Village Fireplace Shuttle Boot Warmers
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
$374 nightly
The price is $402
Nov 22 - Nov 23
Total with taxes and fees
Village Fireplace Shuttle Boot Warmers
A modern kitchen with stainless steel appliances, wooden flooring, and white cabinetry.

9. Rutland apartment on the bus route with central A/C, near Pico

Rutland apartment on the bus route with central A/C, near Pico
Rutland
8.0 out of 10, Very good, (1 review)
"Spotless interior, but the exterior will benifit from a refresh.Conveniently walkable for shops and restaurants."
United States
Thomas A.
$300 nightly
The price is $336
Nov 9 - Nov 10
Total with taxes and fees
Rutland apartment on the bus route with central A/C, near Pico
A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

10. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
$221 nightly
The price is $250
Nov 8 - Nov 9
Total with taxes and fees
Cozy Village Condo-Okemo Shuttle
A spacious restaurant with high ceilings, exposed ductwork, and a mix of wooden and metal furniture.

11. Killington resort: Walk to Mountain, Ski/Ride, World Cup

Killington resort: Walk to Mountain, Ski/Ride, World Cup
Killington
9.8 out of 10, Exceptional, (38 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
$314 nightly
The price is $355
Nov 8 - Nov 9
Total with taxes and fees
Killington resort: Walk to Mountain, Ski/Ride, World Cup
A sign for Whiffletree with a snowboard illustration, indicating a possible winter sports area.

12. Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"The property was a great location. Close enough for a daily drive to stowe or woodstock. I would highly recommend this place. The only thing I wish I would have known is there are a few flights of stairs to go up and down with luggage. Thanks for a great stay"
United States
Brandy
$333 nightly
The price is $376
Nov 8 - Nov 9
Total with taxes and fees
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
Aerial view

13. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$427 nightly
The price is $470
Nov 10 - Nov 11
Total with taxes and fees
The Suites at Killington Center
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

14. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
Rutland
9.4 out of 10, Exceptional, (6 reviews)
"Perfect spot for a large group to enjoy Rutland, Killington, and the surrounding area. Plenty of beds for everyone, and bathrooms so no one felt cramped whatsoever. Beautiful home and safe neighborhood. All around a great stay. If we come back for the US Open of MTB next year, this house would be high on our list to stay in again."
United States
Matthew T.
$722 nightly
The price is $816
Nov 8 - Nov 9
Total with taxes and fees
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A kitchen with granite countertops, wooden cabinets, and a built-in oven.

15. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (22 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
$383 nightly
The price is $433
Nov 8 - Nov 9
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

16. 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, (24 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
$489 nightly
The price is $553
Nov 8 - Nov 9
Total with taxes and fees
New Ludlow Village Home with Stunning Okemo Mountain View
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

17. 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, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
$427 nightly
The price is $458
Nov 17 - Nov 18
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

18. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$202 nightly
The price is $228
Nov 11 - Nov 12
Total with taxes and fees
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
A hot tub with a mountain view, surrounded by snow-covered trees and a wooden structure.

19. Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals

Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals
Killington
9.8 out of 10, Exceptional, (70 reviews)
"Excellent location and hosts would definitely recommend! House is perfect "
United States
Tim C.
$1,000 nightly
The price is $1,130
Nov 8 - Nov 9
Total with taxes and fees
Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals
A hot tub with a view of a green landscape through large windows.

20. Rabbit Hole Trail Creek, Pool, Hot Tub, Fireplace

Rabbit Hole Trail Creek, Pool, Hot Tub, Fireplace
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Our hosts were super communicative. The check in process was smooth. The condo was clean and well appointed. Beds good. Our hosts even gave us some local coffee and maple syrup as a welcome gift (along with a few other things). Definitely recommend "
United States
Amy G.
$514 nightly
The price is $560
Nov 8 - Nov 9
Total with taxes and fees
Rabbit Hole Trail Creek, Pool, Hot Tub, 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.
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Top Cuttingsville Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"
Rachel 1-night trip
Posted 1 day ago
On The River Inn

Find out more about Cuttingsville

Everything you need to know about Cuttingsville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttingsville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cuttingsville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cuttingsville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cuttingsville rentals

At Expedia, we put the best Cuttingsville vacation 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 vacation.

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 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 Buttermilk Falls. In the larger area, you’ll find Shrewsbury Free Library and Killington Peak.

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.