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Oldtown Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Oldtown holiday rentals

A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

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 HK$941
HK$1,579 total
includes taxes & fees
2 Sept - 3 Sept
Oldtown Guesthouse
A bed with a dark quilted cover, two beige pillows, and a headboard with two wall-mounted lamps.

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 HK$1,113
HK$1,258 total
includes taxes & fees
4 Sept - 5 Sept
Canal Cabins
A kitchen with white tiled backsplash, wooden shelves holding glassware, and a coffee maker on the counter.

3. 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, (120 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 HK$1,452
HK$2,469 total
includes taxes & fees
2 Sept - 3 Sept
Secluded, romantic cabin with hot tub on 12 acres of woodland.
A small attic bedroom with a sloped ceiling, a single bed, and a window.

4. 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 HK$572
HK$1,473 total
includes taxes & fees
9 Sept - 10 Sept
Primitive Cozy Tiny Cabin with Starlink internet
A garden with a variety of flowers and plants, a wooden structure, and a white fence.

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, (48 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
The price is HK$941
HK$1,521 total
includes taxes & fees
2 Sept - 3 Sept
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
An outdoor wooden deck with seating, a large tree, and a glass-enclosed room with a bench.

6. 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, (42 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 HK$1,121
HK$2,646 total
includes taxes & fees
8 Sept - 9 Sept
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
A grassy field with a wooden fence and trees in the background.

7. 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, (17 reviews)
"The tiny house was very clean, we were able to message the host easily."
United States
Brenda B.
The price is HK$1,098
HK$1,466 total
includes taxes & fees
8 Sept - 9 Sept
Charming Cottage on 15 Acre Farm near Romney, WV
A wooden cabin with a porch, a green door, and a window.

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 HK$980
HK$1,360 total
includes taxes & fees
15 Sept - 16 Sept
1/2 of a double cabin with one king sized bed (sleeps 2)
A covered patio with a table and chairs, a hanging basket, and a satellite dish.

9. 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, (60 reviews)
"Host was very polite and helpful!"
United States
Quintin
The price is HK$941
HK$1,380 total
includes taxes & fees
2 Sept - 3 Sept
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
A high-ceilinged room with large windows, a wooden interior, a sofa, a coffee table, and a fireplace.

10. 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 HK$1,446
HK$2,934 total
includes taxes & fees
28 Sept - 29 Sept
Upscale w Fireplace, Fire Pit, Games in Gated Comm
A rustic cabin interior with a stone fireplace, leather furniture, and a view of the outdoors.

11. 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 HK$1,582
HK$3,314 total
includes taxes & fees
7 Sept - 8 Sept
Waterfront cabin w/ workspace & BBQ 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 HK$1,068
HK$2,269 total
includes taxes & fees
15 Sept - 16 Sept
Log Cabin w Loft, Grill, Deck, Fire Pit, & WiFi
A natural setting with a body of water, trees, and a sandy area.

13. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$690
HK$1,734 total
includes taxes & fees
2 Sept - 3 Sept
Fox Burrow @ Timber Ridge Retreat
A wooden gate in a garden with lush greenery and flowering plants.

14. 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, (27 reviews)
"Clean cozy room, functional kitchen and the host was communicative! "
United States
Carrie S.
The price is HK$531
HK$1,472 total
includes taxes & fees
3 Sept - 4 Sept
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

15. Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!

Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
Cumberland
10.0 out of 10, Exceptional, (10 reviews)
"Easy walk into town and the train station."
United States
Kathy M.
The price is HK$1,214
HK$1,567 total
includes taxes & fees
2 Sept - 3 Sept
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A wooden deck with picnic tables and chairs, a hot tub, and a view of a forest.

16. Huge Cabin w Hot Tub, Deck, Grill & WiFi

Huge Cabin w Hot Tub, Deck, Grill & WiFi
Berkeley Springs
9.6 out of 10, Exceptional, (38 reviews)
"The Bear's Den was the perfect spot for our annual girl's trip! We ended up hiking the trails on the mountain and going to the Old Roman Bath House and Vine Trattoria for dinner Saturday night. Thank you to the host for checking in and attending to our concerns. "
United States
Francesca 'Chessa' B.
Huge Cabin w Hot Tub, Deck, Grill & WiFi
A wooden cabin interior with a dining area, a sofa, and a balcony with a view of the mountains.

17. 3BR cabin w/ scenic deck and pet-friendly

3BR cabin w/ scenic deck and pet-friendly
Great Cacapon
9.0 out of 10, Wonderful, (36 reviews)
"The cabin is so well equipped in the kitchen that it made cooking a breeze! The house was clean and tidy and such a perfect escape for a little getaway to unplug from the busy city hustle and bustle. The deck was fabulous with such amazing views during the day and absolutely stunning stargazing at night! If you’re thinking about it, book it! Wish we could have stayed longer!"
United States
Kristin M.
The price is HK$1,291
HK$2,452 total
includes taxes & fees
7 Sept - 8 Sept
3BR cabin w/ scenic deck and pet-friendly
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

18. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (8 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is HK$1,247
HK$1,695 total
includes taxes & fees
25 Sept - 26 Sept
The Suite On Smallwood
A cozy living room with a stone fireplace, wooden beams, a large window overlooking a forest, and a rustic bar area.

19. 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 HK$1,291
HK$2,452 total
includes taxes & fees
3 Sept - 4 Sept
Cozy cabin w/ hot tub, backyard & BBQ grill
A cabin with a deck, large windows, and a stone foundation.

20. Tucked Away w/Hot Tub, Fire Pit, Deck & WiFi

Tucked Away w/Hot Tub, Fire Pit, Deck & WiFi
Great Cacapon
9.0 out of 10, Wonderful, (17 reviews)
"Perfect weekend getaway"
United States
Anonymous traveller
The price is HK$1,261
HK$2,411 total
includes taxes & fees
15 Sept - 16 Sept
Tucked Away w/Hot Tub, Fire Pit, Deck & WiFi
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

Comfort Inn & Suites LaVale - Cumberland

Comfort Inn & Suites LaVale - Cumberland

10/10 Excellent
"the place was great!! the service and staff very helpful we will stay here again"
RONALD 1-night trip
Posted 13 hours ago
Comfort Inn & Suites LaVale - Cumberland

Find out more about Oldtown

Search for holiday rentals in Oldtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Oldtown using one of the methods below:

  • View our selection of featured holiday rentals in Oldtown
  • Use the map to find apartments and other holiday homes in the Oldtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oldtown while they last

Look no further and take a look at our great range of rental properties in Oldtown!

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?

Cannon Cliffside River Retreat- FREE WIFI: This holiday home rental outside of Oldtown is located on a river, and has a fireplace, a selection of games 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 and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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.