View from the Fort Tower

Holiday Homes in Charlestown

  • 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
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Charlestown holiday homes

Interior

Perfect 2-bedroom in charming Newport

Perfect 2-bedroom in charming Newport
Newport
The price is €190
includes taxes & fees
15 Jun - 16 Jun
Perfect 2-bedroom in charming Newport
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, (110 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is €293
includes taxes & fees
12 Jun - 13 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is €364
includes taxes & fees
14 Jun - 15 Jun
Chic Farmhouse Decor | Deck w/View
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (60 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is €271
includes taxes & fees
15 Jun - 16 Jun
Family Friendly Hilltop House In Putney Vermont
Interior

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
The price is €326
includes taxes & fees
14 Jun - 15 Jun
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (26 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is €305
includes taxes & fees
15 Jun - 16 Jun
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Interior

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, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is €305
includes taxes & fees
29 Jun - 30 Jun
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (4 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.
The price is €387
includes taxes & fees
14 Jun - 15 Jun
Lakefront Family Fun Retreat
Fridge, microwave, oven, stovetop

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is €449
includes taxes & fees
18 Jun - 19 Jun
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is €499
includes taxes & fees
14 Jun - 15 Jun
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is €373
includes taxes & fees
14 Jun - 15 Jun
Charming Chester Farmhouse near Near VT Slopes
Interior

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away
Sunapee
10.0 out of 10, Exceptional, (26 reviews)
"Great location. Great house for a family ski vacation. "
United States
Marianne H.
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away
Shower, soap, shampoo, toilet paper

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (15 reviews)
"Perfect location. Neat place. Very clean!"
United States
Frank F.
The price is €346
includes taxes & fees
9 Jul - 10 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
TV, fireplace, DVD player, stereo

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

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
New London
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic property and host! An excellent home base for skiing at Mt. Sunapee. Especially loved the hot tub and fire pit."
United States
Kurt W.
The price is €1,160
includes taxes & fees
17 Jun - 18 Jun
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"The Treehouse provided an excellent retreat. Beautiful property and excellent hosts. "
United States
T G.
The price is €408
includes taxes & fees
15 Jun - 16 Jun
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Exterior

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (2 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is €697
includes taxes & fees
15 Jun - 16 Jun
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
TV, fireplace, table football, stereo

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is €397
includes taxes & fees
22 Jun - 23 Jun
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
TV, fireplace, DVD player, stereo

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Newbury
10.0 out of 10, Exceptional, (11 reviews)
"We had an amazing stay! The property was beautiful and the hosts were awesome. It was the perfect place to host a big group. We particularly enjoyed the big kitchen for cooking large meals and the outdoor deck seating. This place was great and we would happily stay again!"
United States
Lilly N.
The price is €945
includes taxes & fees
15 Jun - 16 Jun
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Fridge, microwave, oven, stovetop

Boutique Cottage Near Lake Sunapee | Fire Pit + View

Boutique Cottage Near Lake Sunapee | Fire Pit + View
New London
10.0 out of 10, Exceptional, (105 reviews)
"Lovely home. Very clean and nicely renovated. Will stay again when back in the area!"
United States
Cheryl S.
The price is €578
includes taxes & fees
15 Jun - 16 Jun
Boutique Cottage Near Lake Sunapee | Fire Pit + View
TV, fireplace, computer monitors

Elysium on Little Sunapee-Dock, Firepit, Trails

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (14 reviews)
"Great Lake house with all the amenities you need for a great week!! Kitchen is well stocked. Wonderful hosts!"
United States
Caren H.
The price is €806
includes taxes & fees
17 Jun - 18 Jun
Elysium on Little Sunapee-Dock, Firepit, Trails
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
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"The room and common areas were clean and well maintained. The front desk staff were very friendly and helpful when we arrived, which made check-in a pleasant experience. The breakfast was good overall; however, breakfast service ended at 9:00 a.m., and by 8:30 a.m. several items had already run out and were not replenished. Since we arrived late the night before, the early breakfast ending time was a bit challenging for our group. One thing to consider when booking is room location. We stayed on the first floor and could hear quite a bit of noise from the room above us. If noise is a concern, I would recommend requesting a room on the second floor. Overall, we had a positive stay and appreciated the cleanliness and friendly service."
Christina 1-night trip
Posted less than an hour ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
410
Accommodation
455 Holiday Homes
Lowest Price
€190
Highest Price
€1,160