Default HTG hotel image

Cuttingsville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Cuttingsville vacation rentals

Aerial view

1. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is ￥12,435
￥37,080 total
includes taxes & fees
Aug 18 - Aug 19
Mountain Green
Smart TV, fireplace, video games, books

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 ￥24,376
￥82,260 total
includes taxes & fees
Aug 18 - Aug 19
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
House (2 Bedrooms) | Interior

3. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is ￥41,264
￥66,828 total
includes taxes & fees
Aug 19 - Aug 20
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
TV, stereo

4. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is ￥19,118
￥63,708 total
includes taxes & fees
Sep 6 - Sep 7
Killington Retreat | Deck-Fire Pit-Mountain Views!
Private kitchen

5. 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 ￥14,769
￥37,572 total
includes taxes & fees
Aug 18 - Aug 19
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Exterior

6. 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 ￥52,308
￥157,483 total
includes taxes & fees
Aug 31 - Sep 1
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Dining

7. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (5 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is ￥28,104
￥76,405 total
includes taxes & fees
Aug 23 - Aug 24
large ski ranch hot tub close to killington pets ok
Dining

8. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (13 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 ￥15,773
￥34,708 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Rutland Retreat
Property grounds

9. Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is ￥30,574
￥79,923 total
includes taxes & fees
Aug 19 - Aug 20
Modern Farm House…minutes to Okemo; 2 King beds!
TV

10. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is ￥29,275
￥109,481 total
includes taxes & fees
Aug 23 - Aug 24
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Interior

11. Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (86 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.
Perfect Getaway! Cozy, Modern & Convenience to Everything!
Smart TV

12. Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!

Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!
Killington
9.8 out of 10, Exceptional, (188 reviews)
"The condo was in excellent condition and very clean. Great location too. Owner was very responsive. "
United States
Michael V.
The price is ￥21,508
￥27,905 total
includes taxes & fees
Aug 18 - Aug 19
Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!
Condo, 2 Bedrooms | Living area

13. The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
10.0 out of 10, Exceptional, (3 reviews)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is ￥36,994
￥104,437 total
includes taxes & fees
Aug 31 - Sep 1
The Woods by Killington Vacation Rentals - 2 Bedrooms
Indoor pool

14. 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 ￥71,694
￥133,763 total
includes taxes & fees
Aug 21 - Aug 22
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Interior

15. Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
The price is ￥29,364
￥89,257 total
includes taxes & fees
Aug 18 - Aug 19
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Interior

16. SunBear- AC, Pool, Game Room, Fireplace, Hiking!

SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Killington
9.8 out of 10, Exceptional, (31 reviews)
"Very accommodating and helpful hosts"
United States
Sean W.
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Outdoor dining

17. 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 ￥33,766
￥43,167 total
includes taxes & fees
Aug 18 - Aug 19
Okemo | Studio Condo + Loft | Near Slopes + Pool
Indoor pool

18. Sunrise Timberline 3BR ski in/ski out with fireplace, pool and hot tub

Sunrise Timberline 3BR ski in/ski out with fireplace, pool and hot tub
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Excellent location, clean and exactly what you are looking for from a ski/winter get away. "
United States
Joseph C.
Sunrise Timberline 3BR ski in/ski out with fireplace, pool and hot tub
Dining

19. 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, (18 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is ￥42,730
￥94,734 total
includes taxes & fees
Aug 22 - Aug 23
New Ludlow Village Home with Stunning Okemo Mountain View
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cuttingsville Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Very nice hotel"
John 2-night trip
Posted less than an hour ago
Hampton Inn Rutland

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:

  • View our selection of featured holiday rentals in Cuttingsville
  • Use the map to find apartments and other holiday homes in the Cuttingsville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cuttingsville while they last

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

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?

Mountainside 5-BR Ski-In/Out Okemo Villa: This vacation home near Cuttingsville is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 hot tub.

What’s there to see and do in Cuttingsville?

While exploring the area, visit family-friendly sights like Pond Hill Ranch and Pro Rodeo, 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.