Photo by The Curious Zephyr

Search Vacation Homes in Charlestown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Charlestown

Quaint lakefront home with a private deck, firepit, and dock

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 private deck, firepit, and dock

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

8.2 out of 10, Very Good, (39)
"Had a business retreat with 6 associates. The cabin was great and operated as one would expect for a ski cabin. Nice fire place and hot tub. The TVs are older so they have a hard time connecting to the WIFI for Netflix, Prime, etc. I recommend bringing agame console aor "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ski-in/out home with a hot tub, fireplace, cable & golf nearby

9.4 out of 10, Exceptional, (23)
"Nice and roomy. Plenty of room throughout the entire house. Kitchen area LARGE. back deck was nice with the hot tub. Ski run steps from the house. Really nice place."
Ski-in/out home with a hot tub, fireplace, cable & golf nearby

Pet-Friendly Claremont Vacation Rental!

8.8 out of 10, Excellent, (5)
"Only will stay here! "
Pet-Friendly Claremont Vacation Rental!

Heated Saltwater Pool: Riverfront Home in Ludlow

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay. The house was very clean and well maintained and very well stocked. The pool and surrounding area were beautiful. We enjoyed day hikes at buttermilk falls and echo lake, which are so close by. We highly recommend this place to anyone looking to spend a few relaxing days in Vermont."
Heated Saltwater Pool: Riverfront Home in Ludlow

Timeless Red Sox Retreat w/ Scenic Mountain Views!

10.0 out of 10, Exceptional, (22)
"Beautiful property "
Timeless Red Sox Retreat w/ Scenic Mountain Views!

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (5)
"In town for funeral, the place was great. Very roomy and comfy."
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

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

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (14)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is SAR 1,097
SAR 1,801 total
includes taxes & fees
19 Aug - 20 Aug
Downtown Hot Tub Escape

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

10.0 out of 10, Exceptional, (160)
"We love the house, it had everything we needed!"
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

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

9.8 out of 10, Exceptional, (212)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Berry Mountain Lodge: Spacious 5-bedroom house close to skiing and Lake Sunapee

Berry Mountain Lodge: Spacious 5-bedroom house close to skiing and Lake Sunapee

Pristine Waterfront, Charming Home, Breathtaking Views

9.8 out of 10, Exceptional, (57)
"Our trip was wonderful. Very secluded and brought our two small dogs, it was very relaxing and a great get away."
Pristine Waterfront, Charming Home, Breathtaking Views

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

Panoramic Mountain View, Lots To Do, Or Enjoy Doing Nothing

10.0 out of 10, Exceptional, (83)
"Great place to stay with a wonderful view."
Panoramic Mountain View, Lots To Do, Or Enjoy Doing Nothing

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

Brand new Aframe btw Okemo and Killington with a dock on Lake Rescue

10.0 out of 10, Exceptional, (1)
"The house was fantastic, soft furnishings made us feel right at home. Pool room in the basement was great fun. Great location, peaceful, comfortable and immaculately maintained home. Owners were super responsive for any questions and made us feel at ease. Thank you!"
Brand new Aframe btw Okemo and Killington with a dock on Lake Rescue

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views

Okemo Modern Mountain Escape - 5 bedroom, 3 bathroom house

10.0 out of 10, Exceptional, (6)
"Easy to work with the owner. Great house and location."
Okemo Modern Mountain Escape - 5 bedroom, 3 bathroom house

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (26)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Charlestown Hotel Reviews