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Holiday Homes in Charlestown

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Charlestown

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Enjoy cooking in this well-equipped kitchen with a wooden dining table and chairs.

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (39)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Downtown Hot Tub Escape
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and oven, surrounded by dark cabinetry and a wooden countertop.

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is AU$746
includes taxes & fees
11 Aug - 12 Aug
Downtown Hot Tub Escape
Charming Chester Farmhouse – peaceful and close to everything!
Relax in the serene outdoor seating area surrounded by lush greenery and vibrant flowers.

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (12)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is AU$660
includes taxes & fees
8 Aug - 9 Aug
Charming Chester Farmhouse – peaceful and close to everything!
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Enjoy meals in this dining area with a table and chairs, surrounded by a scenic view of a body of water and the snowy landscape.

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

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great place, great host, great location!"
The price is AU$880
includes taxes & fees
3 Sept - 4 Sept
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Alpine 6-BR Estate On Okemo Mountain
Relax in a hot tub surrounded by serene winter scenery.

Alpine 6-BR Estate On Okemo Mountain

10.0 out of 10, Exceptional, (2)
"Nice place"
Alpine 6-BR Estate On Okemo Mountain
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Enjoy cooking in this kitchen with a brick fireplace, large island, and modern appliances.

Timeless Red Sox Retreat w/ Scenic Mountain Views!

10.0 out of 10, Exceptional, (23)
"Beautiful property "
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Stunning two-story home with a charming red door and cozy porch.

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (46)
"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Situated in a secluded wooded area, this cabin offers a traditional two-story retreat with a balcony and multiple windows.

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Set amidst a serene natural landscape, this lodge features a multi-level structure with a distinctive roof and spacious balconies.

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (173)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Quaint lakefront home with a fire pit and beautiful views
Enjoy breathtaking views of the snowy landscape from this deck overlooking the serene surroundings.

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a fire pit and beautiful views
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi
Dining

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

10.0 out of 10, Exceptional, (1)
"This was the definition of a New England inn!! Super cute and the staff were fantastic! They were so helpful! I would definitely stay here again!! "
The price is AU$320
includes taxes & fees
8 Aug - 9 Aug
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi
Cozy cottage tucked away in the woods
Sit by the fire pit surrounded by tall trees in a serene forest setting.

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (43)
"Nice and comfy - loved the decor and the property."
Cozy cottage tucked away in the woods
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!
Stunning two-story building with a grand staircase and large windows, set amidst lush greenery and a natural rock formation.

Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

9.8 out of 10, Exceptional, (161)
"We love the house, it had everything we needed!"
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!
Eastman Home with Hot Tub!
Relax in this spacious living area with a high ceiling, featuring a sofa, coffee table, fireplace, and flat-screen TV.

Eastman Home with Hot Tub!

9.6 out of 10, Exceptional, (14)
"Great place, clean & easy"
Eastman Home with Hot Tub!
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Relax on the deck overlooking the serene lake surrounded by lush greenery.

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (213)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Relax with a drink at the rustic bar, featuring a long counter and stools, shuffleboard table, and vending machine.

Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (27)
"The cabin was perfect. Had everything we might need. Loved the room, views, location, and game room. Thanks so much "
The price is AU$383
includes taxes & fees
17 Aug - 18 Aug
Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Ski Chalet with Hot Tub on Okemo Mountain
Relax in a serene hot tub surrounded by a dense forest, offering an atmosphere for unwinding.

Ski Chalet with Hot Tub on Okemo Mountain

10.0 out of 10, Exceptional, (43)
"Wonderful House - Held 2 Families Perfectly3 min drive to mountain The hot tub is great addition "
Ski Chalet with Hot Tub on Okemo Mountain
Dockside Dream | 4 mins to Mt Sunapee | Dock | VIEWS | Grill
Cozy attic bedroom with two beds, a bedside table, and a window offering a view of the surrounding greenery.

Dockside Dream | 4 mins to Mt Sunapee | Dock | VIEWS | Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"The cottage was the perfect place for a family visit and the hosts were wonderful and helpful! Highly recommend!"
Dockside Dream | 4 mins to Mt Sunapee | Dock | VIEWS | Grill
Charming 4-bedroom Colonial in lovely Keene with WiFi, AC
Relax in this inviting living space with a wooden ceiling, comfortable sofa, and dining area.

Charming 4-bedroom Colonial in lovely Keene with WiFi, AC

10.0 out of 10, Exceptional, (1)
"The home was inviting clean and comfortable. Our inviting, provided us with ample kitchen items, towels, and entertainment in the form of books and extensive library of nostalgic albums and games. There was plenty of parking for four cars in the driveway as well as street parking if needed. The location was perfect for walking into town to enjoy the many restaurants and shops."
Charming 4-bedroom Colonial in lovely Keene with WiFi, AC
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
Laundry room with washer and dryer, adjacent to a patio area with outdoor seating.

Countryside, mountain-view house near eagle's nest with patios - dog-friendly

9.6 out of 10, Exceptional, (5)
"Perfect little spot for a ski trip to Stratton!"
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
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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