Cuttingsville Vacation Rentals

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Our top choices for Cuttingsville vacation rentals

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is CA $73
CA $400 total
includes taxes & fees
May 1 - May 2
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $67
CA $302 total
includes taxes & fees
May 1 - May 2
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is CA $105
CA $255 total
includes taxes & fees
May 3 - May 4
Cozy Rutland Retreat

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is CA $109
CA $263 total
includes taxes & fees
May 3 - May 4
Vermont Double Queen Suite | 10 Mins to Killington

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very good, (39 reviews)
"Great place. Met our needs. "
United States
Sean K.
The price is CA $101
CA $355 total
includes taxes & fees
May 2 - May 3
Cozy condo on ski shuttle route with free WiFi & full ktichen

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.0 out of 10, Good, (48 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is CA $81
CA $322 total
includes taxes & fees
May 2 - May 3
Clean & bright condo with mountain views & modern kitchen - walk to lifts

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, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is CA $103
CA $353 total
includes taxes & fees
May 1 - May 2
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is CA $101
CA $473 total
includes taxes & fees
May 3 - May 4
Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing
Killington
8.2 out of 10, Very good, (35 reviews)
"It was clean and as advertised"
United States
Kiehl H.
Resort condo with balcony & shared seasonal amenities - close to skiing

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very good, (36 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is CA $86
CA $378 total
includes taxes & fees
May 1 - May 2
Comfortable mountain gem with pool, mountain views, & indoor parking space

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is CA $122
CA $419 total
includes taxes & fees
May 1 - May 2
Killington condo 5 min to killington resort

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (32 reviews)
"Great location."
United States
Dustin S.
The price is CA $109
CA $395 total
includes taxes & fees
May 1 - May 2
Welcoming condo near the slopes with free WiFi and full kitchen

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.0 out of 10, Wonderful, (15 reviews)
"The apartment was very comfortable, including a very convenient bathroom. There was everything we needed. Though the apartment did not look like the photo on the internet site. There was no street number on the building which made it difficult to find it. "
United States
lilya l.
The price is CA $109
CA $338 total
includes taxes & fees
May 1 - May 2
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is CA $137
CA $342 total
includes taxes & fees
May 1 - May 2
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

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 CA $122
CA $308 total
includes taxes & fees
May 13 - May 14
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is CA $101
CA $253 total
includes taxes & fees
May 3 - May 4
Vermont Suite | 10 Min to Killington & Woodstock

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is CA $130
CA $403 total
includes taxes & fees
May 4 - May 5
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
The price is CA $171
CA $575 total
includes taxes & fees
May 1 - May 2
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is CA $154
CA $420 total
includes taxes & fees
May 4 - May 5
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is CA $130
CA $288 total
includes taxes & fees
May 4 - May 5
Efficient condo near slopes with kitchenette & great location
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

Find out more about Cuttingsville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cuttingsville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Okemo Mountain Lodging by Vail Resorts: Located near Cuttingsville, this vacation home rental is in the mountains and offers an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

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.