A stone tunnel with greenery on the sides.

Oldtown Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 AU$291
includes taxes & fees
22 Sept - 23 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 AU$213
includes taxes & fees
19 Sept - 20 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 AU$443
includes taxes & fees
14 Sept - 15 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 AU$262
includes taxes & fees
16 Sept - 17 Sept
Primitive Cozy Tiny Cabin with Starlink internet
A wooden cabin with a porch, a green door, and a window.

5. 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 AU$222
includes taxes & fees
14 Sept - 15 Sept
1/2 of a double cabin with one king sized bed (sleeps 2)
A garden with a variety of flowers and plants, a wooden structure, and a white fence.

6. 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 AU$274
includes taxes & fees
13 Sept - 14 Sept
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
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, (18 reviews)
"The tiny house was very clean, we were able to message the host easily."
United States
Brenda B.
The price is AU$264
includes taxes & fees
21 Sept - 22 Sept
Charming Cottage on 15 Acre Farm near Romney, WV
An outdoor wooden deck with seating, a large tree, and a glass-enclosed room with a bench.

8. 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, (44 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 AU$457
includes taxes & fees
15 Sept - 16 Sept
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
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, (61 reviews)
"Host was very polite and helpful!"
United States
Quintin
The price is AU$245
includes taxes & fees
17 Sept - 18 Sept
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
A covered outdoor area with a wooden deck, a sofa with cushions, and a table with chairs.

10. River Cabin w/hot tub, fire pit, deck, games, wifi

River Cabin w/hot tub, fire pit, deck, games, wifi
Great Cacapon
9.2 out of 10, Wonderful, (207 reviews)
"Really enjoyed all of the peaceful nature around the cabin and the screened in porch! Would stay here again "
United States
Marykate S.
The price is AU$553
includes taxes & fees
17 Sept - 18 Sept
River Cabin w/hot tub, fire pit, deck, games, wifi
A wooden staircase leading to a deck overlooking a forested valley with hills in the background.

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 AU$544
includes taxes & fees
13 Sept - 14 Sept
Waterfront cabin w/ workspace & BBQ grill
A high-ceilinged room with large windows, a wooden interior, a sofa, a coffee table, and a fireplace.

12. 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 AU$529
includes taxes & fees
20 Sept - 21 Sept
Upscale w Fireplace, Fire Pit, Games in Gated Comm
A wooden gate in a garden with lush greenery and flowering plants.

13. 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 AU$259
includes taxes & fees
14 Sept - 15 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.

14. 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 AU$280
includes taxes & fees
13 Sept - 14 Sept
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A cozy living room with a stone fireplace, a wooden ceiling, and a loft area with a balcony.

15. 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 AU$401
includes taxes & fees
16 Sept - 17 Sept
Log Cabin w Loft, Grill, Deck, Fire Pit, & WiFi
A living room with a brown leather sofa, a blue couch with patterned pillows, a coffee table, and a wooden floor.

16. Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!

Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Cumberland
9.8 out of 10, Exceptional, (17 reviews)
"Lovely place! "
United States
Courtney N.
The price is AU$272
includes taxes & fees
14 Sept - 15 Sept
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
A rustic log cabin with a green roof, a porch with outdoor seating, and a sign indicating an office entrance.

17. 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 AU$224
includes taxes & fees
13 Sept - 14 Sept
Private cabin with two full beds. ADA accessible.
A natural setting with a body of water, trees, and a sandy area.

18. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$310
includes taxes & fees
16 Sept - 17 Sept
Fox Burrow @ Timber Ridge Retreat
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

19. 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 AU$306
includes taxes & fees
17 Sept - 18 Sept
The Suite On Smallwood
A lodge with a green roof, wooden exterior, and a star emblem. It features a covered porch with chairs and a table, surrounded by a gravel driveway and a forested hillside.

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

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (6 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 AU$222
includes taxes & fees
15 Sept - 16 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

Sleep Inn & Suites Cumberland - LaVale

Sleep Inn & Suites Cumberland - LaVale

10/10 Excellent
"The staff went above and beyond to make our stay wonderful!"
Brandi 2-night trip
Posted 2 hours ago
Sleep Inn & Suites Cumberland - LaVale

Find out more about Oldtown

Everything you need to know about Oldtown 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 Oldtown 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 Oldtown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oldtown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oldtown. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oldtown 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 Oldtown holiday rentals we have selected for you start as low as AU$213 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oldtown rentals

At Expedia, we put the best Oldtown 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 Oldtown 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 Oldtown 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 Oldtown. 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 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?

Historic 1840 year old Farmhouse Homestead in an idyllic, countryside setting: This holiday home rental outside of Oldtown is located on a river, and has a patio, 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 fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.