Default HTG hotel image

Charleston Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Charleston holiday rentals

1. Tall Pines Retreat Escape to our charming chalet tucked away in the forest..

Tall Pines Retreat Escape to our charming chalet tucked away in the forest..
Glenburn
10.0 out of 10, Exceptional, (4 reviews)
"The stay was great! My boyfriend and i planned an ice fishing trip and this place was perfect! Gorgeous, clean and the property owner was super responsive! We will definitely book there again!"
United States
Briana H.
The price is NZ$363
includes taxes & fees
17 Nov - 18 Nov
Tall Pines Retreat Escape to our charming chalet tucked away in the forest..

2. Rustic intown country apartment on the Moosehead trail

Rustic intown country apartment on the Moosehead trail
Sangerville
9.6 out of 10, Exceptional, (48 reviews)
"The place was a very nice place to stay"
United States
Ruth
The price is NZ$213
includes taxes & fees
14 Nov - 15 Nov
Rustic intown country apartment on the Moosehead trail

3. Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn

Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
Glenburn
8.8 out of 10, Excellent, (3 reviews)
"Everything was perfect, If I could recommend one thing it would be free local channels on the tv"
United States
Bruce
The price is NZ$415
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn

4. Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Sangerville
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
The price is NZ$537
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

5. Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly

Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly
Old Town
9.4 out of 10, Exceptional, (13 reviews)
"Very pet friendly!"
United States
Sue H.
The price is NZ$396
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly

6. Pine Tree Retreat

Pine Tree Retreat
Hermon
The price is NZ$811
includes taxes & fees
13 Nov - 14 Nov
Pine Tree Retreat

7. Simple cabin on 26 acres with direct access to ITS and four wheeler trails.

Simple cabin on 26 acres with direct access to ITS and four wheeler trails.
Brownville
9.0 out of 10, Wonderful, (2 reviews)
"The stay at Eric's property was excellent."
United States
Wendy L.
The price is NZ$345
includes taxes & fees
28 Nov - 29 Nov
Simple cabin on 26 acres with direct access to ITS and four wheeler trails.

8. Hermon Pond Studio

Hermon Pond Studio
Hermon
10.0 out of 10, Exceptional, (107 reviews)
"Awesome place to stay very clean, host is super friendly and accommodating."
United States
Douglas C.
The price is NZ$437
includes taxes & fees
15 Nov - 16 Nov
Hermon Pond Studio

9. Four bedroom in United States of America, Orono

Four bedroom in United States of America, Orono
Orono
10.0 out of 10, Exceptional, (4 reviews)
"It was a perfect place for our two families to share! "
United States
Howard W.
The price is NZ$949
includes taxes & fees
27 Nov - 28 Nov
Four bedroom in United States of America, Orono

10. Howland House King bed Seconds from I-95

Howland House King bed Seconds from I-95
2.5 star property
Howland
Howland House King bed Seconds from I-95

11. MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,

MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,
Bangor
10.0 out of 10, Exceptional, (51 reviews)
"Enjoyed the property, close to things we wanted to do in the area."
United States
rick r.
The price is NZ$476
includes taxes & fees
13 Dec - 14 Dec
MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,

12. Velvet Pine Haven. Private Retreat on Quiet Lane

Velvet Pine Haven. Private Retreat on Quiet Lane
Bangor
9.6 out of 10, Exceptional, (4 reviews)
"Plenty of space for our trip!"
United States
Nicole E.
The price is NZ$531
includes taxes & fees
15 Nov - 16 Nov
Velvet Pine Haven. Private Retreat on Quiet Lane

13. Charming studio in Bangor Maine on Broadway park.

Charming studio in Bangor Maine on Broadway park.
Bangor
9.8 out of 10, Exceptional, (35 reviews)
"It was a perfect nest for us with a great experience, the host was really friendly and charming. The downtown proximity was great to walk. Thank you for your hospitality."
Canada
Bernard
The price is NZ$288
includes taxes & fees
30 Nov - 1 Dec
Charming studio in Bangor Maine on Broadway park.

14. Cozy Hermon Pond Basecamp: 15m to Bangor Airport, Fast Wi-Fi & Winter Ready

Cozy Hermon Pond Basecamp: 15m to Bangor Airport, Fast Wi-Fi & Winter Ready
Hermon
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay! Host was so accommodating to our needs! "
United States
Nicole T.
The price is NZ$436
includes taxes & fees
23 Nov - 24 Nov
Cozy Hermon Pond Basecamp: 15m to Bangor Airport, Fast Wi-Fi & Winter Ready

15. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (25 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is NZ$1,025
includes taxes & fees
13 Nov - 14 Nov
Peaceful, Spacious Lodge with Golf & Sunset Views

16. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (2 reviews)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is NZ$521
includes taxes & fees
20 Nov - 21 Nov
Pretty Old House in Newport

17. The Raven's Nest in Maine!

The Raven's Nest in Maine!
Milford
The price is NZ$305
includes taxes & fees
13 Nov - 14 Nov
The Raven's Nest in Maine!

18. Field of Dreams Tiny Home w/ Jacuzzi & Personal Theater

Field of Dreams Tiny Home w/ Jacuzzi & Personal Theater
Bangor
The price is NZ$430
includes taxes & fees
13 Dec - 14 Dec
Field of Dreams Tiny Home w/ Jacuzzi & Personal Theater

19. Quiet Orono Getaway • 2 Min to I-95 & Downtown

Quiet Orono Getaway • 2 Min to I-95 & Downtown
Orono
The price is NZ$862
includes taxes & fees
13 Nov - 14 Nov
Quiet Orono Getaway • 2 Min to I-95 & Downtown
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 Charleston Hotel Reviews

Find out more about Charleston

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Charleston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Charleston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Charleston. Seeing all the best attractions is bound to make you fall in love with Charleston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Charleston short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Charleston?

Yes, there are holiday rentals close to the most popular sights in Charleston, or you can select a more secluded option if you're looking for a relaxing stay.

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

Big Red House - Historic Bangor Home : This holiday home rental outside of Charleston is located on a river, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 4 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 garden and a selection of games.

What can I see and do in Charleston?

Explore the area and family-friendly sights such as Piscatiquis County Ice Arena, or get out into nature at a spot like Pushaw Lake. In the wider area, you’ll find Sebec Lake and Peaks-Kenny State Park.

What are holiday rentals like in Charleston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Charleston. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.