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

Condo, 1 Bedroom | Exterior
Mountain Green Resort by Killington VR - 1 Bedrooms

Condo in Killington

Mountain Green Resort by Killington VR - 1 Bedrooms
3.5 star property
The price is ￥22,347
￥71,317 total
includes taxes & fees
Dec 15 - Dec 16
Mountain Green Resort by Killington VR - 1 Bedrooms
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥13,061
￥44,745 total
includes taxes & fees
Dec 16 - Dec 17
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Cottage in Ludlow

Ludlow Ski Cabin 2 Mi to Ski Parking
3.0 star property
The price is ￥28,455
￥56,931 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ludlow Ski Cabin 2 Mi to Ski Parking
Internet, bed sheets
Efficient condo near slopes with kitchenette & great location

Apartment in Ludlow

Efficient condo near slopes with kitchenette & great location
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 ￥14,772
￥35,135 total
includes taxes & fees
Dec 17 - Dec 18
Efficient condo near slopes with kitchenette & great location
Smart TV, fireplace
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

Condo in The Woods

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
2.0 star property
10.0 out of 10, Exceptional, (3)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
The price is ￥24,459
￥70,487 total
includes taxes & fees
Dec 15 - Dec 16
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Interior
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cottage in Mendon

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
2.0 star property
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
The price is ￥21,209
￥63,952 total
includes taxes & fees
Dec 15 - Dec 16
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Exterior
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Chalet in Plymouth

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is ￥27,848
￥84,653 total
includes taxes & fees
Dec 16 - Dec 17
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Interior
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo in Ludlow

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is ￥10,729
￥52,340 total
includes taxes & fees
Dec 16 - Dec 17
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Exterior
Killington Studio: Great Location! Comfy. 431

Condo in Killington

Killington Studio: Great Location! Comfy. 431
8.8 out of 10, Excellent, (5)
"Great place to stay!"
United States
Carla M.
The price is ￥11,631
￥36,685 total
includes taxes & fees
Dec 15 - Dec 16
Killington Studio: Great Location! Comfy. 431
Condo, 1 Bedroom, Kitchen, Garden View | Private kitchen | Mini-fridge, microwave, oven, cookware/dishes/utensils
The Suites at Killington Center

Condo in Killington

The Suites at Killington Center
3.5 star property
The price is ￥21,271
￥57,606 total
includes taxes & fees
Dec 15 - Dec 16
The Suites at Killington Center
Dining
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Condo in The Woods

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
3.0 star property
9.8 out of 10, Exceptional, (6)
"Very clean and well equipped condo! We enjoyed our stay."
United States
Tanya W.
The price is ￥24,288
￥73,446 total
includes taxes & fees
Dec 15 - Dec 16
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
Indoor pool, a heated pool
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Condo in Killington

Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!
9.6 out of 10, Exceptional, (5)
"My friends and I enjoyed it solid spot for a skiing weekend"
United States
Matt M.
The price is ￥18,814
￥49,214 total
includes taxes & fees
Dec 15 - Dec 16
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!
1 bedroom, iron/ironing board, internet, bed sheets
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Condo in Ludlow

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is ￥15,704
￥40,865 total
includes taxes & fees
Dec 17 - Dec 18
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Exterior
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Condo in Killington

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is ￥14,772
￥44,360 total
includes taxes & fees
Dec 15 - Dec 16
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Property grounds
Ben & Jerry Suite | Skiing | Hiking | Biking

Apartment in Bridgewater

Ben & Jerry Suite | Skiing | Hiking | Biking
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is ￥17,726
￥36,561 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Ben & Jerry Suite | Skiing | Hiking | Biking
Property grounds
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Condo in Clock Tower Base Area

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.2 out of 10, Wonderful, (25)
"Loved the location"
United States
Steven W.
The price is ￥20,525
￥54,565 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Restaurant
Mountain Green Resort

Apartment in Killington

Mountain Green Resort
4.0 star property
The price is ￥40,178
￥91,487 total
includes taxes & fees
Dec 15 - Dec 16
Mountain Green Resort
1 bedroom, desk, iron/ironing board, free WiFi
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Condo in Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is ￥20,354
￥47,966 total
includes taxes & fees
Dec 15 - Dec 16
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Smart TV, fireplace
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Cabin in Killington

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
The price is ￥25,485
￥78,908 total
includes taxes & fees
Dec 15 - Dec 16
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is ￥33,586
￥56,070 total
includes taxes & fees
Dec 14 - Dec 15
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Yea"
Robert Miller 1-night trip
Posted 8 hours ago
Pointe at Castle Hill Resort

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.