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In two months
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Apr 17 - Apr 19

Our top choices for Charlestown vacation homes

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Brook Road Condo

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
$296 nightly
The price is $321
Dec 24 - Dec 25
Total with taxes and fees
Brook Road Condo
Comfort Townhome | Private kitchen | Full-size fridge, microwave, oven, stovetop
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
$276 nightly
The price is $299
Dec 24 - Dec 25
Total with taxes and fees
Brook Road Condo
Property grounds
Book your ski vacations for the upcoming season.

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.
$352 nightly
The price is $381
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book your ski vacations for the upcoming season.
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
$264 nightly
The price is $287
Jan 11 - Jan 12, 2026
Total with taxes and fees
Downtown Hot Tub Escape
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.
$420 nightly
The price is $456
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chic Farmhouse Decor | Deck w/View
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

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (18)
"We loved sitting by and listening to the river. Everything was as described."
United States
Jennifer A.
$367 nightly
The price is $398
Jan 11 - Jan 12, 2026
Total with taxes and fees
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Interior
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.
$181 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Fridge, microwave, oven, stovetop
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.
$362 nightly
The price is $393
Jan 12 - Jan 13, 2026
Total with taxes and fees
Lake Front Family Friendly Escape
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

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
$592 nightly
The price is $642
Jan 8 - Jan 9, 2026
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$254 nightly
The price is $285
Jan 5 - Jan 6, 2026
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
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

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.
$439 nightly
The price is $496
Dec 25 - Dec 26
Total with taxes and fees
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Terrace/patio
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.
$299 nightly
The price is $335
Jan 7 - Jan 8, 2026
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Exterior
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.
$446 nightly
The price is $484
Jan 4 - Jan 5, 2026
Total with taxes and fees
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Outdoor dining
Charming Home Walk to Downtown!

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.
$571 nightly
The price is $620
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming Home Walk to Downtown!
TV, fireplace, DVD player, books
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
New London
10.0 out of 10, Exceptional, (14)
"Something for everyone! Not only will we be returning, but highly recommend! "
United States
Hillary N.
$1,009 nightly
The price is $1,095
Dec 28 - Dec 29
Total with taxes and fees
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
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

@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.
$555 nightly
The price is $602
Dec 30 - Dec 31
Total with taxes and fees
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (1)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
$553 nightly
The price is $600
Dec 24 - Dec 25
Total with taxes and fees
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (104)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
$468 nightly
The price is $511
Jan 13 - Jan 14, 2026
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Newbury
10.0 out of 10, Exceptional, (9)
"Very spacious, with beautiful amenities and very friendly hosts!"
United States
Matthew H.
$960 nightly
The price is $1,042
Jan 4 - Jan 5, 2026
Total with taxes and fees
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
$992 nightly
The price is $1,111
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
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 Charlestown Hotel Reviews

Best Western Springfield Hotel

Best Western Springfield Hotel

10/10 Excellent
"The greeting from staff was lovely. My room was neat and well stocked with toiletries. "
Kathleen 2-night trip
Posted 4 days ago
Best Western Springfield Hotel

Find out more about Charlestown

Charlestown Vacation Homes information

Number of reviews
411
Accommodation
434 Vacation Homes
Lowest Price
$203
Highest Price
$1,111

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