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

Charlestown Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Charlestown holiday rentals

A red house with a covered porch and a chimney.

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, (172 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 HK$1,334
HK$2,908 total
includes taxes & fees
23 Sept - 24 Sept
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

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 HK$941
HK$3,218 total
includes taxes & fees
23 Sept - 24 Sept
Lakefront Family Fun Retreat
A two-story house with a deck, surrounded by dense forest.

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,229
HK$7,838 total
includes taxes & fees
23 Sept - 24 Sept
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is HK$1,640
HK$3,312 total
includes taxes & fees
29 Sept - 30 Sept
Charming Chester Farmhouse near Near VT Slopes
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

5. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,561
HK$3,168 total
includes taxes & fees
23 Sept - 24 Sept
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A spacious living area with hardwood flooring, a staircase, a black entertainment unit, a door, and a window with blinds.

6. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
The price is HK$2,353
HK$2,792 total
includes taxes & fees
23 Sept - 24 Sept
Explore the upper valley from this spacious Claremont Home
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

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 HK$437
HK$2,324 total
includes taxes & fees
30 Sept - 1 Oct
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

8. 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 HK$1,440
HK$2,346 total
includes taxes & fees
27 Sept - 28 Sept
Brook Road Cabin
A two-story house with a porch, a staircase, and a front door.

9. 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 HK$824
HK$2,129 total
includes taxes & fees
23 Sept - 24 Sept
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

10. 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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is HK$404
HK$1,821 total
includes taxes & fees
23 Sept - 24 Sept
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A garden with purple flowers and a river in the background.

11. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is HK$1,236
HK$2,271 total
includes taxes & fees
23 Sept - 24 Sept
Family Friendly Hilltop House In Putney Vermont
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

12. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is HK$1,684
HK$2,263 total
includes taxes & fees
22 Oct - 23 Oct
Fat Sheep Farm & Cabins
A covered porch with wicker furniture, a table, and chairs.

13. 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 HK$1,655
HK$4,604 total
includes taxes & fees
20 Oct - 21 Oct
Terrific 3-bedroom cottage with AC in charming Cavendish
A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

14. 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 HK$1,334
HK$2,520 total
includes taxes & fees
4 Oct - 5 Oct
Brook Road Cabin
A two-story house with a porch, a staircase, and a front door.

15. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is HK$783
HK$1,872 total
includes taxes & fees
23 Sept - 24 Sept
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A golf course with a winding path, trees, and a distant mountain range.

16. 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 HK$783
HK$1,819 total
includes taxes & fees
23 Sept - 24 Sept
Efficient condo near slopes with kitchenette & great location
A cabin with a large, curved roof and a smaller adjacent structure, surrounded by dense forest and mountains in the background.

17. 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 HK$1,412
HK$2,482 total
includes taxes & fees
23 Sept - 24 Sept
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

18. 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 HK$2,605
HK$4,946 total
includes taxes & fees
8 Oct - 9 Oct
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A forested area with a gravel path leading to a cabin with a metal roof and a wooden deck.

19. Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (26 reviews)
"The place was clean and very comfortable"
United States
Pam D.
The price is HK$1,483
HK$3,831 total
includes taxes & fees
23 Sept - 24 Sept
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

20. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
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 HK$1,553
HK$3,235 total
includes taxes & fees
23 Sept - 24 Sept
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
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

Fullerton Inn

Fullerton Inn

8/10 Good
"The Owner was an amazing guy. We had to cancel a 2nd room for friends last minute and he was so caring and did not hesitate to help. Its a cute old inn."
Debbie 2-night trip
Posted 16 hours ago
Fullerton Inn

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 holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay. Charlestown is known for its university setting and museums.

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

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Charlestown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Charlestown?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Charlestown stay.

What’s there to see and do in Charlestown?

Connecticut River State Park and Connecticut River 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 holiday rental in Charlestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlestown. Holiday rentals provide amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.