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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (174 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 AU$511
includes taxes & fees
27 Oct - 28 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A spacious living area with hardwood flooring, a staircase, a black entertainment unit, a door, and a window with blinds.

2. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
10.0 out of 10, Exceptional, (1 review)
"Nice place."
United States
Michael R.
The price is AU$512
includes taxes & fees
24 Oct - 25 Oct
Explore the upper valley from this spacious Claremont Home
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

3. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
The price is AU$578
includes taxes & fees
2 Nov - 3 Nov
Lakefront Family Fun Retreat
Dining

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 AU$588
includes taxes & fees
12 Nov - 13 Nov
Charming Chester Farmhouse near Near VT Slopes
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

5. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (14 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is AU$253
includes taxes & fees
3 Nov - 4 Nov
Fat Sheep Farm & Cabins
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

6. 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 AU$426
includes taxes & fees
2 Nov - 3 Nov
Brook Road Cabin
A two-story house with a deck, surrounded by dense forest.

7. 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 AU$1,378
includes taxes & fees
4 Nov - 5 Nov
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A covered porch with wicker furniture, a table, and chairs.

8. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Cavendish
10.0 out of 10, Exceptional, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is AU$718
includes taxes & fees
4 Nov - 5 Nov
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A wooden cabin interior with a staircase leading to a loft, a kitchen area, and large windows offering views of the surrounding forest.

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

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is AU$567
includes taxes & fees
11 Nov - 12 Nov
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Exterior

10. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is AU$1,021
includes taxes & fees
29 Oct - 30 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

11. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (25 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is AU$751
includes taxes & fees
24 Oct - 25 Oct
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

12. 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 AU$457
includes taxes & fees
26 Oct - 27 Oct
Brook Road Cabin
A lakeside view with a wooden deck, picnic table, and benches.

13. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is AU$483
includes taxes & fees
27 Oct - 28 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A golf course with a winding path, trees, and a hilly landscape.

14. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is AU$430
includes taxes & fees
24 Oct - 25 Oct
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A wooden cabin interior with a staircase, a sofa, and a table.

15. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (57 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is AU$568
includes taxes & fees
22 Nov - 23 Nov
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

16. Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is AU$410
includes taxes & fees
23 Nov - 24 Nov
Brook Road Condo
A yellow building with a porch and a sign that reads "Brook Road Inn."

17. Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Nice place for a mountain stay"
United States
Meghan B.
The price is AU$449
includes taxes & fees
25 Oct - 26 Oct
Brook Road Condo
A two-story house with a porch, a staircase, and a front door.

18. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is AU$382
includes taxes & fees
27 Oct - 28 Oct
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
A large hotel with multiple buildings, a pond, and a white fence.

19. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
Brownsville
The price is AU$403
includes taxes & fees
28 Oct - 29 Oct
2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

20. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is AU$389
includes taxes & fees
29 Oct - 30 Oct
Cozy cabin in charming Londonderry
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

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

10/10 Excellent
"The check in process was great.There was 24 hour coffee.Our room was spacious and it had a record player with 3 classic albums...one by Little Feat that we played.There were many other albums available in the living room near the entrance.We were happy to have been able to go on a boat cruise that included dinner and a lovely sunset.There were other nice places to eat.We really enjoyed our one day stay and will come again!"
Gloria 1-night trip
Posted 8 hours ago
Hideaway Inn Mt.Sunapee

Find out more about Charlestown

Everything you need to know about Charlestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Charlestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Charlestown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Charlestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charlestown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charlestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charlestown holiday rentals we have selected for you start as low as AU$253 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Charlestown rentals

At Expedia, we put the best Charlestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Charlestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Charlestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Charlestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.