Ascutney Vacation Rentals

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Our top choices for Ascutney vacation rentals

Vacation Home in Goshen

Brook Road Condo
3.0 star property
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
$276 nightly
The price is $299
Dec 22 - Dec 23
Total with taxes and fees
Brook Road Condo

Vacation Home in Newport

Lake Front Family Friendly Escape
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
$340 nightly
The price is $369
Dec 22 - Dec 23
Total with taxes and fees
Lake Front Family Friendly Escape
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$297 nightly
The price is $335
Jan 11 - Jan 12, 2026
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
$181 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
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
$215 nightly
The price is $235
Jan 12 - Jan 13, 2026
Total with taxes and fees
Ben & Jerry’s Studio | 10 Min to Killington

Cabin in Goshen

Brook Road Cabin
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
$296 nightly
The price is $321
Dec 22 - Dec 23
Total with taxes and fees
Brook Road Cabin
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
$481 nightly
The price is $539
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
$328 nightly
The price is $371
Jan 5 - Jan 6, 2026
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$321 nightly
The price is $350
Jan 12 - Jan 13, 2026
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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.
$519 nightly
The price is $581
Jan 12 - Jan 13, 2026
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Cottage in Goshen

Brook Road Cabin
3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
$282 nightly
The price is $306
Dec 22 - Dec 23
Total with taxes and fees
Brook Road Cabin
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
$166 nightly
The price is $188
Dec 22 - Dec 23
Total with taxes and fees
Addie's Place: A Quiet and Quirky Private Guesthouse
10.0 out of 10, Exceptional, (18)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
$614 nightly
The price is $666
Jan 1 - Jan 2, 2026
Total with taxes and fees
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
$286 nightly
The price is $323
Jan 5 - Jan 6, 2026
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.8 out of 10, Exceptional, (14)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
$172 nightly
The price is $188
Dec 22 - Dec 23
Total with taxes and fees
Treehouse at Wise Pines- NoBo
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$361 nightly
The price is $395
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
10.0 out of 10, Exceptional, (26)
"Great stay. Had a wonderful time."
United States
Chris P.
$446 nightly
The price is $484
Jan 4 - Jan 5, 2026
Total with taxes and fees
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Vacation Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$300 nightly
The price is $336
Jan 7 - Jan 8, 2026
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
9.2 out of 10, Wonderful, (25)
"Loved the location"
United States
Steven W.
$299 nightly
The price is $338
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Vacation Home in Sunapee

Chic Farmhouse Decor | Deck w/View
10.0 out of 10, Exceptional, (51)
"This place is pristine and very cozy. Bed's are insanely comfortable too. Will definitely try to stay there again. "
United States
Peter S.
$420 nightly
The price is $456
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chic Farmhouse Decor | Deck w/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 Ascutney Hotel Reviews

Find out more about Ascutney

Everything you need to know about Ascutney vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ascutney vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ascutney vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ascutney vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ascutney. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ascutney in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ascutney rentals

At Expedia, we put the best Ascutney vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ascutney rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ascutney vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ascutney. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Ascutney?

Yes, we have vacation rentals near top attractions in Ascutney, or you can choose a more secluded option if you'd like a relaxing place to stay. Ascutney is known for its mountain views and ski areas.

What's the top vacation rental in Ascutney?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This vacation home rental outside of Ascutney 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 can I see and do in Ascutney?

Connecticut River and Romaine Tenney Memorial Park are a couple of lovely local spots to get outside and enjoy nature. While here, Weathersfield Proctor Library and Wilgus State Park are other places worth a visit.

What are vacation rentals like in Ascutney?

Vacation rentals are privately owned properties you can book for several days or more in Ascutney. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip.