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Oldtown Holiday Rentals

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Our top choices for Oldtown holiday rentals

1. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
The price is NZ$356
includes taxes & fees
22 Sept - 23 Sept
Oldtown Guesthouse

2. Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (17 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
United States
Nebojsa
The price is NZ$266
includes taxes & fees
2 Oct - 3 Oct
Canal Cabins

3. Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
10.0 out of 10, Exceptional, (13 reviews)
"Always a great stay. Peaceful and plenty to explore. We cant wait to come back!"
United States
Anthony A.
The price is NZ$327
includes taxes & fees
21 Sept - 22 Sept
Primitive Cozy Tiny Cabin with Starlink internet

4. Secluded, romantic cabin with hot tub on 12 acres of woodland.

Secluded, romantic cabin with hot tub on 12 acres of woodland.
Cumberland
10.0 out of 10, Exceptional, (121 reviews)
"Everything we expected and more. Visited relatively early in the Spring so we're coming back in June to make better use of outdoor dining, etc. The cabin was super cozy and we made full use of the hot tub and fireplace. We really enjoyed our stay."
United States
Steven H.
The price is NZ$695
includes taxes & fees
12 Oct - 13 Oct
Secluded, romantic cabin with hot tub on 12 acres of woodland.

5. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (50 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
The price is NZ$326
includes taxes & fees
21 Sept - 22 Sept
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

6. Charming Cottage on 15 Acre Farm near Romney, WV

Charming Cottage on 15 Acre Farm near Romney, WV
Romney
10.0 out of 10, Exceptional, (18 reviews)
"The tiny house was very clean, we were able to message the host easily."
United States
Brenda B.
The price is NZ$317
includes taxes & fees
28 Sept - 29 Sept
Charming Cottage on 15 Acre Farm near Romney, WV

7. Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /

Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
Cumberland
10.0 out of 10, Exceptional, (62 reviews)
"Host was very polite and helpful!"
United States
Quintin
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /

8. 1/2 of a double cabin with one king sized bed (sleeps 2)

1/2 of a double cabin with one king sized bed (sleeps 2)
Flintstone
10.0 out of 10, Exceptional, (1 review)
"If you’re looking for a quiet peaceful cabin to just go get lost in the world of your significant other, this is the place to go! They’re far enough from the everyday life but still close enough to enjoy all the beauty of their charming city!! The food is to die for and definitely a reason for us to return!! Nothing bad to say at all except they need larger hot water tanks bc when I’m enjoying my wife that includes sharing a shower that we would have preferred not to be rushed out of!! Otherwise...
United States
LaRon G.
The price is NZ$299
includes taxes & fees
28 Sept - 29 Sept
1/2 of a double cabin with one king sized bed (sleeps 2)

9. Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit

Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
Springfield
10.0 out of 10, Exceptional, (45 reviews)
"Excellent stay at this cabin, extremely clean, smooth check in and out process, and all amenities were available plus a well stocked kitchen. Highly recommended stay for a nice quiet getaway. "
United States
Alex K.
The price is NZ$571
includes taxes & fees
21 Sept - 22 Sept
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit

10. Stunning Mountain Views w/Deck & Grill on 5 Acres!

Stunning Mountain Views w/Deck & Grill on 5 Acres!
Slanesville
9.6 out of 10, Exceptional, (4 reviews)
"The perfect get away. From sunsets to sunrise, star gazing, and grilling on the porch with an incredible view of the valley. Will have to come back for the fall foliage!"
United States
Manuel D.
The price is NZ$607
includes taxes & fees
22 Sept - 23 Sept
Stunning Mountain Views w/Deck & Grill on 5 Acres!

11. Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
Berkeley Springs
9.0 out of 10, Wonderful, (28 reviews)
"Clean cozy room, functional kitchen and the host was communicative! "
United States
Carrie S.
The price is NZ$310
includes taxes & fees
21 Sept - 22 Sept
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

12. Log Cabin w Loft, Grill, Deck, Fire Pit, & WiFi

Log Cabin w Loft, Grill, Deck, Fire Pit, & WiFi
Great Cacapon
9.0 out of 10, Wonderful, (32 reviews)
"Great stay will do again hot tub was very nice. The bed was super comfy "
United States
michael t.
The price is NZ$485
includes taxes & fees
27 Sept - 28 Sept
Log Cabin w Loft, Grill, Deck, Fire Pit, & WiFi

13. Upscale w Fireplace, Fire Pit, Games in Gated Comm

Upscale w Fireplace, Fire Pit, Games in Gated Comm
Paw Paw
9.8 out of 10, Exceptional, (9 reviews)
"Loved our stay overall. Beautiful decor, cozy and remote location. Great communication with host as well. Perfect spot to get away from the hustle and stresses of daily work life. "
United States
Jella S.
The price is NZ$676
includes taxes & fees
21 Sept - 22 Sept
Upscale w Fireplace, Fire Pit, Games in Gated Comm

14. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$385
includes taxes & fees
21 Sept - 22 Sept
Fox Burrow @ Timber Ridge Retreat

15. Waterfront cabin w/ workspace & BBQ grill

Waterfront cabin w/ workspace & BBQ grill
Paw Paw
9.8 out of 10, Exceptional, (21 reviews)
"Beautiful view of the river. "
United States
Doreen K.
The price is NZ$773
includes taxes & fees
14 Oct - 15 Oct
Waterfront cabin w/ workspace & BBQ grill

16. 3BR cabin w/ scenic deck and pet-friendly

3BR cabin w/ scenic deck and pet-friendly
Great Cacapon
9.0 out of 10, Wonderful, (39 reviews)
"We had a nice time at the cabin even with wild swings in the weather from 80degrees to 40 over the course of 3 days. The cabin stayed comfortable and we had no trouble with check in, the hot tub, or anything else. It was a beautiful place to stay with lots of good birdwatching. "
United States
Alison A.
The price is NZ$534
includes taxes & fees
24 Sept - 25 Sept
3BR cabin w/ scenic deck and pet-friendly

17. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (9 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is NZ$333
includes taxes & fees
19 Oct - 20 Oct
The Suite On Smallwood

18. Cozy cabin w/ hot tub, backyard & BBQ grill

Cozy cabin w/ hot tub, backyard & BBQ grill
Great Cacapon
9.0 out of 10, Wonderful, (19 reviews)
"Great place! "
United States
Rebecca S.
The price is NZ$517
includes taxes & fees
21 Sept - 22 Sept
Cozy cabin w/ hot tub, backyard & BBQ grill

19. Private cabin with two full beds. ADA accessible.

Private cabin with two full beds. ADA accessible.
Flintstone
10.0 out of 10, Exceptional, (7 reviews)
"This cabin has all the necessities, is in a great location and is clean and well maintained. Absolutely perfect for a couple and close to lots of outdoor activities! Will absolutely stay here in the future."
United States
Leah I.
The price is NZ$299
includes taxes & fees
30 Sept - 1 Oct
Private cabin with two full beds. ADA accessible.

20. Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (7 reviews)
"Weve stayed here before, enroute to visit family in Maryland. The cabins are very amply large, with modern ammenities. The beds were comfy, eating area was clean and spacious, with even a well thought out large front porch, with a rocking chair to enjoy the serenity of the distant mountains. We'll be back!"
Canada
Karl
The price is NZ$277
includes taxes & fees
21 Sept - 22 Sept
Private cabin with two double beds (sleep 4)
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 Oldtown Hotel Reviews

Find out more about Oldtown

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?

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi: This holiday home rental outside of Oldtown is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Oldtown?

While you're exploring the area, Potomac River and Lake Habeeb Beaches are a couple of picturesque spots to get outside and enjoy nature. Chesapeake and Ohio Canal and Paw Paw Tunnel are a couple of places you'll find in the wider area.

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.