Photo by Kayla Berry

Oldtown Holiday Rentals

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Holiday Rentals in Oldtown

Secluded, romantic cabin with hot tub on 12 acres of woodland.
10.0 out of 10, Exceptional, (59)
"The secluded cabin was a perfect place to rest after hiking and biking. We appreciated the cleanliness of the cabin, as well as how tastefully it was decorated. Will definitely recommend this VRBO to friends. The only possible suggestion I can think to offer is perhaps some lounge chairs for the deck."
The price is NZ$545
per night
1 Jul - 2 Jul
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Perched in the Trees, Very Private, Screened in Porch with view
9.8 out of 10, Exceptional, (98)
"What a cozy little surprise this cabin was. Everything you'll need is at your finger tips and town is just a few minutes up the road if you forget something. A great hide away for two or a small family. And if you're thinking about tiny living, rent this cute little place first."
The price is NZ$311
per night
23 Jun - 24 Jun
Perched in the Trees, Very Private, Screened in Porch with view
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.4 out of 10, Exceptional, (9)
"I would consider changing carpet to vinyl flooring. Good location if you love to golf."
The price is NZ$485
per night
25 Jun - 26 Jun
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
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Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (51)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
Hot Tub, Private Lake, & Huge Deck at Chalet Cabin
9.2 out of 10, Wonderful, (20)
"It was nice to get away and relax in a secluded location. Enjoyed the hot tub. Had a good time walking around Berkeley Springs (even though most shops were closed). All in all it was a nice time away from work and hectic life."
The price is NZ$690
per night
26 Jun - 27 Jun
Hot Tub, Private Lake, & Huge Deck at Chalet Cabin
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
The price is NZ$822
per night
6 Jul - 7 Jul
Dreamtime - Modern A-frame Cabin w/ Hot tub
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
9.0 out of 10, Wonderful, (16)
"Quaint home in the woods. Perfect for our weekend away. Loved the hot tub and firepit."
The price is NZ$518
per night
9 Jul - 10 Jul
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (245)
"Perfect for a quiet getaway. Complete relaxation"
The price is NZ$514
per night
20 Jun - 21 Jun
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!
8.4 out of 10, Very good, (27)
"This Coolfont cabin was the perfect weekend home for our family of four (and our dog). Friendly staff at the lodge welcomed us with giant smiles and answered all our of questions. The cabin was cozy and warm with ample space. Large, clean bathrooms. Especially loved the wood stove. We enjoyed the hiking and biking trails nearby, as well as the on-site restaurant, on-site pool and brew pub just across the street. Will definitely be back!"
Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
9.6 out of 10, Exceptional, (150)
"Most of our stay was on the property. The amenities were great. The game room was nice. The town was very nice and friendly. The food was good."
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
9.8 out of 10, Exceptional, (208)
"Beautiful cabin in a peaceful area. Just what we wanted"
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Couples Cabin - 5 Mi to DT Berkeley Springs!
10.0 out of 10, Exceptional, (57)
"Our stay was outstanding. The accommodations were perfect for a weekend couple get-away in the woods. Our unit was clean and very well furnished and decorated. The surrounding property was spectacular. We had the pleasure to meet the really nice hosts, and even got to tour the other rentals on the property. We will definitely be returning in a future visit to Berkely Springs. Fun little town. Take a hot mineral bath at the Spa just like George Washington."
Couples Cabin - 5 Mi to DT Berkeley Springs!
Hot Tub, Screened Porch, Fire Pit at River Cabin
9.4 out of 10, Exceptional, (20)
"We stayed for a quick last minute getaway. Lots of value for the price. The house was well stocked with necesseties and mostly clean. It could use a more regular deep clean as the windwsills by the kids bed had old bugs, cobwebs on some decor and under the couch trundle bed was very dirty. There wasnt wifi and the number that was left for us couldnt be used on the house phone. None of this hindered our stay though. Hot tub was the reason we booked and very easy to use and enjoy. no neighbors on...
The price is NZ$432
per night
23 Jun - 24 Jun
Hot Tub, Screened Porch, Fire Pit at River Cabin
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
9.8 out of 10, Exceptional, (172)
"Beautiful house and setting in nature. A wonderful relaxing couple of days."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Little cute house close to C&O canal
8.0 out of 10, Very good, (3)
"I felt very cozy and comfortable in this small home, at the top of the hill (great views). Everything was arranged just right. Communication with the host was very easy. I would happily return. Beth"
The price is NZ$259
per night
30 Jun - 1 Jul
Little cute house close to C&O canal
Cabin w Hot Tub, Huge Deck, Firepit & WiFi!
10.0 out of 10, Exceptional, (12)
"We had a great time exploring the region from Spleepy Hollow. The hot tub after a long hike is always great!"
The price is NZ$443
per night
24 Jun - 25 Jun
Cabin w Hot Tub, Huge Deck, Firepit & WiFi!
Awesome New Property/ CANAL RIVER RETREAT
9.8 out of 10, Exceptional, (92)
"Great piece of property"
Awesome New Property/ CANAL RIVER RETREAT
Cozy 3 bedroom, 2 bath pet friendly cabin retreat
9.8 out of 10, Exceptional, (25)
"Had a wonderful time great place to stay"
The price is NZ$650
per night
24 Jun - 25 Jun
Cozy 3 bedroom, 2 bath pet friendly cabin retreat
A luxurious cabin quietly tucked away in the woods, pet friendly, WiFi
10.0 out of 10, Exceptional, (177)
"Beautiful cabin and location. Spotless and super well-stocked with everything you could possibly need for a great stay at Buck Haven."
A luxurious cabin quietly tucked away in the woods, pet friendly, WiFi
Family Oasis with Fire Pit, Close To Hiking
10.0 out of 10, Exceptional, (6)
"This cabin was the perfect size for our family, so comfortable and had all the modern amenities needed while still being in the mountains. Close enough to Berkley Springs (20 minute drive) with cute shops ad restaurants. We would definitely stay again!"
Family Oasis with Fire Pit, Close To Hiking
Don't see what you're looking for?
See all available properties in Oldtown
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.

Other types of properties in Oldtown you may be interested in

Rocky Gap Casino & Resort
3.0 star property
8.8 out of 10, Excellent, (1003)
"Took a long time to get food at the sports bar. Burger was excellent when it did arrive. Staff was very accommodating. Dropped my wedding band behind the dresser and could not get it out. Two staff members came up and moved it late at night to retrieve it for me. I was so grateful. "
The price is NZ$282
per night
8 Jul - 9 Jul
Rocky Gap Casino & Resort
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
The price is NZ$822
per night
6 Jul - 7 Jul
Dreamtime - Modern A-frame Cabin w/ Hot tub
Ramada by Wyndham Cumberland Downtown
3.0 star property
7.0 out of 10, Good, (1000)
"Staying in the Cumberland area overnight as part of a longer trip. I am a train buff and normally request an upper floor room with a view of the railroad tracks that pass nearby whenever I stay at this hotel. For whatever reason, the usual room location was unavailable and I was given a 3rd floor room at the opposite end of the building and the view out the window was almost totally obscured by trees. Room was comfortable, clean, had microwave cable TV and mini-fridge which served my needs...
The price is NZ$159
per night
18 Jul - 19 Jul
Ramada by Wyndham Cumberland 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.

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 Oldtown 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 Oldtown. 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 Oldtown. Seeing all the best attractions is bound to make you fall in love with Oldtown. 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 Oldtown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Oldtown?

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

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

Charming mountaintop cabin with hot tub, pool table, and breathtaking views: This holiday home rental outside of Oldtown is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with an arcade/games room and 1 hot tub.

What’s there to see and do in Oldtown?

Potomac River and Chesapeake and Ohio Canal National Historical Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Paw Paw Tunnel and Chesapeake and Ohio Canal.

What’s a holiday rental in Oldtown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oldtown. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for families.

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