Ascutney Vacation Rentals

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Dec 21 - Dec 22
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Dec 22 - Dec 23
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Dec 26 - Dec 28
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Jan 2 - Jan 4

Our top choices for Ascutney vacation rentals

Comfort Townhome | In-room dining
Brook Road Condo

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
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
The price is ￥29,026
￥47,240 total
includes taxes & fees
Dec 22 - Dec 23
Brook Road Condo
Property grounds
Lake Front Family Friendly Escape

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
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.
The price is ￥19,877
￥58,196 total
includes taxes & fees
Dec 22 - Dec 23
Lake Front Family Friendly Escape
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 ￥18,615
￥52,889 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Dining
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn
Chester Depot
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.
The price is ￥20,350
￥31,979 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Whimsical Room & Private Bathroom in Historic Inn
Property grounds
Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
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 ￥17,984
￥37,092 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Ben & Jerry’s Studio | 10 Min to Killington
TV
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
The price is ￥26,818
￥50,663 total
includes taxes & fees
Dec 22 - Dec 23
Brook Road Cabin
Outdoor pool, a heated pool
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is ￥47,325
￥84,983 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Golf
Well-appointed studio right downtown - less than a mile to Okemo Mountain

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
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is ￥21,612
￥58,514 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Smart TV, fireplace, books
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
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.
The price is ￥29,657
￥55,272 total
includes taxes & fees
Jan 12 - Jan 13, 2026
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Exterior
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
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 ￥36,440
￥96,290 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
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
Brook Road Cabin
Interior
Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse
Hartford
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
The price is ￥15,144
￥29,591 total
includes taxes & fees
Dec 22 - Dec 23
Addie's Place: A Quiet and Quirky Private Guesthouse
TV, fireplace, books
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
2.0 star property
Sunapee
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.
The price is ￥53,951
￥105,094 total
includes taxes & fees
Jan 1 - Jan 2, 2026
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Exterior detail
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

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, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is ￥22,716
￥51,008 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Property grounds
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
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
The price is ￥23,663
￥29,680 total
includes taxes & fees
Dec 22 - Dec 23
Treehouse at Wise Pines- NoBo
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is ￥38,333
￥62,361 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Newbury
10.0 out of 10, Exceptional, (26)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is ￥42,593
￥76,339 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Fridge, microwave, oven, stovetop
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
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.
The price is ￥22,085
￥53,004 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Chester Farmhouse Ski Retreat near Slopes
Property grounds
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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, (25)
"Loved the location"
United States
Steven W.
The price is ￥19,246
￥53,288 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Fridge, microwave, oven, stovetop
Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
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.
The price is ￥34,705
￥71,887 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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

Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

10/10 Excellent
"Courteous staff, clean and convenient "
Sheila 2-night trip
Posted 21 hours ago
Courtyard by Marriott Hanover Lebanon

Find out more about Ascutney

Search for holiday rentals in Ascutney on Expedia! You can easily find your home rentals, villas, holiday apartments in Ascutney using one of the methods below:

  • View our selection of featured holiday rentals in Ascutney
  • Use the map to find apartments and other holiday homes in the Ascutney neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ascutney while they last

Look no further and take a look at our great range of rental properties in Ascutney!

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.