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Ascutney Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Ascutney vacation rentals

A large, multi-story hotel with a central courtyard and a reflective water feature.

1. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
Brownsville
$242 nightly
The price is $264
Sep 9 - Sep 10
Total with taxes and fees
2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
A spacious living area with hardwood flooring, a staircase, a black entertainment unit, a door, and a window with blinds.

2. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
$343 nightly
The price is $372
Sep 8 - Sep 9
Total with taxes and fees
Explore the upper valley from this spacious Claremont Home
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

3. Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit

Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit
Cavendish
10.0 out of 10, Exceptional, (53 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
$367 nightly
The price is $396
Sep 15 - Sep 16
Total with taxes and fees
Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

4. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
$286 nightly
The price is $312
Sep 17 - Sep 18
Total with taxes and fees
Fat Sheep Farm & Cabins
A covered porch with wicker furniture, a table, and chairs.

5. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$540 nightly
The price is $605
Sep 8 - Sep 9
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
A two-story house with a deck, surrounded by dense forest.

6. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
$901 nightly
The price is $1,009
Sep 14 - Sep 15
Total with taxes and fees
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A person standing on a sandy beach by a river with trees in the background.

7. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
$466 nightly
The price is $527
Sep 9 - Sep 10
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

8. 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, (24 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
$483 nightly
The price is $541
Sep 8 - Sep 9
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

9. Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access

Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
Cavendish
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$329 nightly
The price is $352
Sep 8 - Sep 9
Total with taxes and fees
Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

10. Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!

Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!
Cavendish
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
$329 nightly
The price is $352
Sep 8 - Sep 9
Total with taxes and fees
Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!
A cabin with a large, curved roof and a smaller adjacent structure, surrounded by dense forest and mountains in the background.

11. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
$280 nightly
The price is $316
Sep 8 - Sep 9
Total with taxes and fees
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A red house with a covered porch and a chimney.

12. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (172 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
$330 nightly
The price is $370
Sep 8 - Sep 9
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

13. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"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.
$380 nightly
The price is $412
Sep 28 - Sep 29
Total with taxes and fees
Lakefront Family Fun Retreat
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

14. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 reviews)
"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
Sep 8 - Sep 9
Total with taxes and fees
Brook Road Cabin
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

15. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (18 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
$529 nightly
The price is $598
Sep 8 - Sep 9
Total with taxes and fees
New Ludlow Village Home with Stunning Okemo Mountain View
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

16. Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
$281 nightly
The price is $310
Sep 8 - Sep 9
Total with taxes and fees
Okemo | Studio Condo + Loft | Near Slopes + Pool
A spacious living room with a stone fireplace, wooden furniture, and large windows.

17. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
$617 nightly
The price is $691
Sep 8 - Sep 9
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A modern living room with a fireplace, a dining area, and a kitchen in the background.

18. Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
$364 nightly
The price is $411
Sep 8 - Sep 9
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

19. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
$380 nightly
The price is $426
Sep 8 - Sep 9
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, under a high ceiling with skylights.

20. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
$743 nightly
The price is $840
Sep 8 - Sep 9
Total with taxes and fees
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
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

The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 7 hours ago
The Jackson

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 $230 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.

Explore a world of travel with Expedia

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?

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock: This vacation home rental outside of Ascutney is located on a river and has an outdoor pool, a fireplace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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.