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Cuttingsville Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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 AED 287
AED 855 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 628
AED 1,966 total
includes taxes & fees
26 Aug - 27 Aug
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 AED 951
AED 1,541 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 441
AED 1,469 total
includes taxes & fees
6 Sep - 7 Sep
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 AED 340
AED 866 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 1,206
AED 3,631 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 648
AED 1,761 total
includes taxes & fees
23 Aug - 24 Aug
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 AED 364
AED 800 total
includes taxes & fees
14 Sep - 15 Sep
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.
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 AED 675
AED 2,524 total
includes taxes & fees
23 Aug - 24 Aug
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 AED 496
AED 643 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 853
AED 2,408 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 1,653
AED 3,084 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 677
AED 2,058 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 778
AED 995 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 985
AED 2,196 total
includes taxes & fees
28 Aug - 29 Aug
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.
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Top Cuttingsville Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Very nice hotel"
John 2-night trip
Posted 3 hours ago
Hampton Inn Rutland

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.