Holiday Homes in Charlestown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Featured Holiday Homes in Charlestown

Comfort Townhome | Private kitchen
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 AU$436
includes taxes & fees
11 Dec - 12 Dec
Brook Road Condo
TV
Brook Road Condo

Brook Road Condo

Goshen
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
The price is AU$475
includes taxes & fees
14 Dec - 15 Dec
Brook Road Condo
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Keene
9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
The price is AU$428
includes taxes & fees
4 Dec - 5 Dec
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop
Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View

Sunapee
10.0 out of 10, Exceptional, (51)
"The house was cozy, peaceful and convenient to skiing. "
United States
Megan D.
The price is AU$675
includes taxes & fees
4 Dec - 5 Dec
Chic Farmhouse Decor | Deck w/View
Exterior
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 AU$659
includes taxes & fees
7 Dec - 8 Dec
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Fridge, microwave, oven, stovetop
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 AU$565
includes taxes & fees
11 Dec - 12 Dec
Lake Front Family Friendly Escape
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (57)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is AU$438
includes taxes & fees
8 Dec - 9 Dec
Family Friendly Hilltop House In Putney Vermont
Interior
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 AU$312
includes taxes & fees
4 Dec - 5 Dec
Whimsical Room & Private Bathroom in Historic Inn
Dining
@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 AU$662
includes taxes & fees
8 Dec - 9 Dec
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Property grounds
Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.

Sutton
10.0 out of 10, Exceptional, (9)
"House is very clean and comfortable. Kitchen well appointed, Nice location with view of Blaisdell Lake. Several state parks and Lake Sunapee nearby"
United States
Nancy B.
The price is AU$596
includes taxes & fees
9 Dec - 10 Dec
Book your ski vacations for the upcoming season.
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Walpole
10.0 out of 10, Exceptional, (50)
"Worked out perfectly for us!"
United States
Andrew P.
The price is AU$855
includes taxes & fees
4 Dec - 5 Dec
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish
9.6 out of 10, Exceptional, (4)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
The price is AU$450
includes taxes & fees
8 Dec - 9 Dec
The Dorothy-10 minutes from Okemo- freshly renovated
Interior
Charming Cavendish Guesthouse

Charming Cavendish Guesthouse

Cavendish
9.8 out of 10, Exceptional, (7)
"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."
United States
deborah m.
The price is AU$452
includes taxes & fees
9 Dec - 10 Dec
Charming Cavendish Guesthouse
Interior
Beautiful home offering privacy on 7 acres with private pond

Beautiful home offering privacy on 7 acres with private pond

West Windsor
10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
United States
Roy S.
The price is AU$794
includes taxes & fees
5 Dec - 6 Dec
Beautiful home offering privacy on 7 acres with private pond
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
Londonderry
8.0 out of 10, Very good, (1)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is AU$758
includes taxes & fees
15 Dec - 16 Dec
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Exterior
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Newport
9.8 out of 10, Exceptional, (17)
"We loved sitting by and listening to the river. Everything was as described."
United States
Jennifer A.
The price is AU$575
includes taxes & fees
15 Dec - 16 Dec
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Outdoor dining
Charming Home Walk to Downtown!

Charming Home Walk to Downtown!

Keene
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is AU$999
includes taxes & fees
4 Dec - 5 Dec
Charming Home Walk to Downtown!
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (16)
"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 AU$535
includes taxes & fees
8 Dec - 9 Dec
Chester Farmhouse Ski Retreat near Slopes
Property grounds
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow
9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
The price is AU$666
includes taxes & fees
8 Dec - 9 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior
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, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AU$666
includes taxes & fees
8 Dec - 9 Dec
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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.
View all properties

Black Friday Sale

Save up to 40% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlestown Hotel Reviews

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

10/10 Excellent
"Yes"
James 1-night trip
Posted 4 days ago
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
478
Accommodation
430 Holiday Homes
Lowest Price
AU$312
Highest Price
AU$999

Explore a world of travel with Expedia