A grassy field with a wooden fence, surrounded by autumn-colored trees and a hill in the background.

Charlestown Vacation Rentals

  • 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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Charlestown vacation rentals

Exterior

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (170 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is ￥26,819
￥57,424 total
includes taxes & fees
Aug 12 - Aug 13
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Property grounds

2. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 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 ￥18,931
￥65,216 total
includes taxes & fees
Sep 1 - Sep 2
Lakefront Family Fun Retreat
Dining

3. 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 ￥32,972
￥67,496 total
includes taxes & fees
Aug 17 - Aug 18
Charming Chester Farmhouse near Near VT Slopes
Property grounds

4. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is ￥11,761
￥42,004 total
includes taxes & fees
Aug 16 - Aug 17
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Interior

5. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (48 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
The price is ￥30,921
￥60,807 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
TV, DVD player

6. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is ￥8,361
￥37,179 total
includes taxes & fees
Sep 9 - Sep 10
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV, DVD player, books, video library

7. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is ￥8,779
￥45,668 total
includes taxes & fees
Aug 18 - Aug 19
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Exterior

8. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is ￥21,298
￥40,824 total
includes taxes & fees
Aug 18 - Aug 19
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Golf

9. Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is ￥15,737
￥48,706 total
includes taxes & fees
Aug 12 - Aug 13
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Exterior

10. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is ￥16,565
￥42,818 total
includes taxes & fees
Aug 12 - Aug 13
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

11. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is ￥35,496
￥95,413 total
includes taxes & fees
Aug 12 - Aug 13
Terrific 3-bedroom cottage with AC in charming Cavendish
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

12. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
The price is ￥27,073
￥45,122 total
includes taxes & fees
Aug 12 - Aug 13
Brook Road Cabin
Exterior

13. Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is ￥85,048
￥159,392 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Vermont Cabin · Mountain Views · Near Okemo
Interior

14. Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is ￥30,290
￥52,294 total
includes taxes & fees
Aug 18 - Aug 19
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Terrace/patio

15. 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, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ￥63,104
￥117,422 total
includes taxes & fees
Sep 3 - Sep 4
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
TV

16. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
The price is ￥26,819
￥51,351 total
includes taxes & fees
Aug 13 - Aug 14
Brook Road Cabin
Golf

17. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is ￥15,737
￥36,583 total
includes taxes & fees
Aug 17 - Aug 18
Efficient condo near slopes with kitchenette & great location
TV, books

18. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is ￥43,924
￥52,281 total
includes taxes & fees
Aug 12 - Aug 13
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV

19. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is ￥22,406
￥71,025 total
includes taxes & fees
Sep 9 - Sep 10
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Interior

20. Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
The price is ￥27,608
￥56,566 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
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

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

10/10 Excellent
"Property was as described. Clean and safe- with a large room. Bare minimum decor and furniture. No dressers or anywhere to put your stuff. There is no staff to speak of except early mornings with cleaning people there. Which feels a bit weird. But room was clean and bed was very comfortable."
Katharine 2-night trip
Posted 3 hours ago
Hideaway Inn Mt.Sunapee

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
  • Use the map to find apartments and other holiday homes in the Charlestown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

Frequently asked questions

Can I find a vacation rental in Charlestown?

Yes, we offer vacation rentals close to the most popular sights in Charlestown, or you can go with a more remote option if you want a relaxing place to stay. Charlestown is known for its university setting and museums.

What are some of the best vacation rentals that Charlestown has to offer?

Okemo Mountain Lodging by Vail Resorts: You might like this vacation home rental near Charlestown. It is in the mountains and offers cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

What’s there to see and do in Charlestown?

Connecticut River and Connecticut River State Park are a couple of scenic spots to enjoy the outdoors, whereas The Fort at No.4 Open Air Museum is one of the cultural attractions. Charlestown Town Hall and Silsby Free Public Library are other places to visit while you're in town.

What’s a vacation rental in Charlestown like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Charlestown. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.