Cuttingsville Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Cuttingsville vacation rentals

Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
Killington
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Indoor pool
Mountain Green

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is ￥34,693
￥46,539 total
includes taxes & fees
Dec 15 - Dec 16
Mountain Green
Interior
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
Killington
The price is ￥25,562
￥63,440 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥13,082
￥41,304 total
includes taxes & fees
Dec 16 - Dec 17
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
1 bedroom, free WiFi, bed sheets
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.4 out of 10, Exceptional, (3)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
The price is ￥23,361
￥30,002 total
includes taxes & fees
Dec 14 - Dec 15
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
3 bedrooms, internet, bed sheets
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Andover
9.0 out of 10, Wonderful, (29)
"Really nice house in a beautiful place. We had a great time. Plenty of space with multiple bedrooms and bathrooms are great. Great kitchen and grill made it easy to feed lots of people. Also lots of great things to do in the house already. One criticism for me was the screen doors. They were not all set in the rails and some of them had holes that let bugs in. It got a bit warm in the house during the day time with no air conditioning so it would’ve been better if the screen doors were...
United States
Dan T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
TV, fireplace, DVD player, books
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Killington
9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
United States
Shawn C.
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Tinmouth
10.0 out of 10, Exceptional, (179)
"Beautiful log cabin near mountains. Quiet and relaxing vacation to get away from it all. "
United States
Sandra B.
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Smart TV, fireplace, video games, DVD player
The Cabin that brings people together

The Cabin that brings people together

The Cabin that brings people together
Bridgewater
9.6 out of 10, Exceptional, (82)
"This was our 3rd visit for an annual family reunion. Nice house with great space, and the yard is a great space to really spread out. The manager is very responsive and checks in periodically; they really want you to have a great stay. I highly recommend this vacation rental, and we’ll be back!"
United States
Peter L.
The Cabin that brings people together
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Ludlow
8.0 out of 10, Very Good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Outdoor pool, a heated pool
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Charming mountain retreat with pool, fire pit, glamping loft, and endless views
Weston
9.8 out of 10, Exceptional, (9)
"An absolutely incredible home and property for a week long end of summer vacation. The setting, atmosphere, decor and attention to detail were all top notch and we couldn’t have been happier. We particularly loved the layout and all of the amenities. This property is a true winner for any season, and we cannot wait to return for a winter retreat! "
United States
Chris L.
Charming mountain retreat with pool, fire pit, glamping loft, and endless views
Interior
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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, (31)
"Very nice property. Full of extra touches (hot tub, virtual fireplace). I appreciated access to a laundry facility. Highly recommend this property."
United States
Julie C.
The price is ￥34,574
￥57,206 total
includes taxes & fees
Dec 16 - Dec 17
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Indoor pool
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Killington
8.2 out of 10, Very Good, (38)
"Room was constantly too hot. Otherwise a great stay"
United States
Cameron M.
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Fridge, microwave, oven, stovetop
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Killington
9.8 out of 10, Exceptional, (60)
"Ski in/ Ski out Great locationJoel was very helpful and friendly. Really enjoyed our stay. "
United States
cynthia c.
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Exterior
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
killington
9.6 out of 10, Exceptional, (17)
"Great place to stay. Central location, bedrooms spacious and common areas w/plenty of space to hang out."
United States
Scott B.
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Exterior
Killington Retreat

Killington Retreat

Killington Retreat
2.0 star property
Killington
9.8 out of 10, Exceptional, (17)
"It was clean and check-in was simple. "
United States
David M.
Killington Retreat
Dining
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ludlow
9.4 out of 10, Exceptional, (41)
"Lovely property and great location to outdoor activities."
United States
Ellen C.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Ludlow
9.6 out of 10, Exceptional, (129)
"Beautiful place! Enjoyed our stay!"
United States
Cathy B.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Internet, bed sheets
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is ￥14,795
￥35,191 total
includes taxes & fees
Dec 17 - Dec 18
Efficient condo near slopes with kitchenette & great location
1 bedroom, internet, bed sheets
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing
Cavendish
8.8 out of 10, Excellent, (9)
"Close to skiing"
United States
Donna
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing
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

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
Bradford 2-night trip
Posted 4 days ago
Mountain Sports Inn

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:

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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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This vacation home rental near Cuttingsville is located on the waterfront and has a balcony, a garden, 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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

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.