Charlestown Holiday Rentals

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Holiday Rentals in Charlestown

Condo in Clock Tower Base Area

9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is NZ$442
includes taxes & fees
1 Dec - 2 Dec
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Holiday Home in Andover

9.0 out of 10, Wonderful, (29)
"Really enjoyed the place for a quiet weekend together."
United States
Eric B.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Holiday Home in Ludlow

8.0 out of 10, Very good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Cabin in Alstead

10.0 out of 10, Exceptional, (12)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is NZ$590
includes taxes & fees
30 Nov - 1 Dec
Owl's Nest Treehouse

Aparthotel in Clock Tower Base Area

4.0 star property
8.8 out of 10, Excellent, (25)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo

Cottage in New London

9.6 out of 10, Exceptional, (47)
"Really clean, comfortable country cottage. Pleased with our stay. 😁"
United States
Jonathan
The price is NZ$253
includes taxes & fees
8 Dec - 9 Dec
Hideaway Cottages, Cottage A

Holiday Home in Ludlow

9.8 out of 10, Exceptional, (127)
"Beautiful place! Enjoyed our stay!"
United States
Cathy B.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Cottage in New London

10.0 out of 10, Exceptional, (25)
"Cozy cabin, easy check in, Wifi available."
United States
Marian R.
The price is NZ$328
includes taxes & fees
8 Dec - 9 Dec
Hideaway Cottages, Cottage B

Cabin in Cavendish

10.0 out of 10, Exceptional, (30)
"Beautiful property and excellent accommodations"
United States
Anthony W.
The price is NZ$626
includes taxes & fees
2 Dec - 3 Dec
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cabin in Cavendish

2.0 star property
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is NZ$618
includes taxes & fees
8 Dec - 9 Dec
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Holiday Home in Ludlow

9.6 out of 10, Exceptional, (171)
"House and grounds were well maintained. "
United States
Dorothy Y.
Idyllic Lakefront House Suited Two Families

Cabin in Londonderry

8.6 out of 10, Excellent, (8)
"We had a wonderful stay."
United States
Joshua
The price is NZ$989
includes taxes & fees
2 Dec - 3 Dec
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Holiday Home in Townshend

10.0 out of 10, Exceptional, (6)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Holiday Home in Ludlow

9.8 out of 10, Exceptional, (40)
"Had a great and comfortable stay with family. House is clean and had all the amenities and supplies needed. "
United States
Aruna G.
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Aparthotel in Clock Tower Base Area

4.0 star property
8.0 out of 10, Very good, (31)
"Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also."
United States
Larry
Solitude Village at Okemo

Cabin in Ludlow

9.8 out of 10, Exceptional, (179)
"Great stay, for a golf trip with 12 guys, there was plenty of room for everyone, would definitely recommend and will be trying to come back and stay as well!"
United States
Matt C.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Cabin in Woodstock

9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
The price is NZ$326
includes taxes & fees
1 Dec - 2 Dec
Treehouse at Wise Pines- NoBo

Cabin in Ludlow

10.0 out of 10, Exceptional, (95)
"We had a lovely time. The cabin is cozy and quiet and being on the lake was wonderful. "
United States
Leah C.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Cottage in Ludlow

9.6 out of 10, Exceptional, (19)
"The house, its location, and dock are real nice. Would come here again."
United States
Wendy G.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Cabin in Woodstock

9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is NZ$326
includes taxes & fees
1 Dec - 2 Dec
Treehouse at Wise Pines- SoBo
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

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 favorite 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 depends 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 NZ$253 per night. Entering your travel dates in the search wizard you might find 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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Charlestown is located on the waterfront, and has a balcony, a garden 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. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What’s there to see and do in Charlestown?

Connecticut River and Swan Commons 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.