A stone tunnel with greenery on the sides.

Oldtown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Oldtown vacation 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.
$195 nightly
The price is $207
Aug 24 - Aug 25
Total with taxes and fees
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
$133 nightly
The price is $151
Sep 15 - Sep 16
Total with taxes and fees
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, (119 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.
$286 nightly
The price is $323
Aug 24 - Aug 25
Total with taxes and fees
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, (12 reviews)
"Always a great stay. Peaceful and plenty to explore. We cant wait to come back!"
United States
Anthony A.
$175 nightly
The price is $195
Sep 1 - Sep 2
Total with taxes and fees
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)
"House was very clean and comfortable, and very convenient to downtown Cumberland. "
United States
Larry M.
$183 nightly
The price is $194
Aug 27 - Aug 28
Total with taxes and fees
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.

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, (17 reviews)
"Was a wonderful cabin, plan to go back every year"
United States
Ken H.
$170 nightly
The price is $189
Aug 31 - Sep 1
Total with taxes and fees
Charming Cottage on 15 Acre Farm near Romney, WV
A pond with cattails and a white boat.

7. BIG D's POND & North Branch of the Potomac river Camping.

BIG D's POND & North Branch of the Potomac river Camping.
Cumberland
10.0 out of 10, Exceptional, (3 reviews)
"Big D'S Pond is beautiful and the owner, is very kind and helpful. We had an amazing time!"
United States
Mary G.
$107 nightly
The price is $114
Aug 25 - Aug 26
Total with taxes and fees
BIG D's POND & North Branch of the Potomac river Camping.
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, (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.
$335 nightly
The price is $338
Aug 26 - Aug 27
Total with taxes and fees
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
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.

9. 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
$168 nightly
The price is $169
Aug 25 - Aug 26
Total with taxes and fees
Private cabin with two double beds (sleep 4)

10. 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, (31 reviews)
"Great stay will do again hot tub was very nice. The bed was super comfy "
United States
michael t.
$269 nightly
The price is $289
Aug 24 - Aug 25
Total with taxes and fees
Log Cabin w Loft, Grill, Deck, Fire Pit, & WiFi
A natural setting with a body of water, trees, and a sandy area.

11. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
$209 nightly
The price is $221
Aug 24 - Aug 25
Total with taxes and fees
Fox Burrow @ Timber Ridge Retreat
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

12. 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.
$177 nightly
The price is $200
Aug 24 - Aug 25
Total with taxes and fees
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A covered patio with a table and chairs, a hanging basket, and a satellite dish.

13. 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, (59 reviews)
"Host was very polite and helpful!"
United States
Quintin
$166 nightly
The price is $176
Aug 26 - Aug 27
Total with taxes and fees
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.

14. 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.
$358 nightly
The price is $388
Sep 1 - Sep 2
Total with taxes and fees
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.

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.
$388 nightly
The price is $421
Aug 30 - Aug 31
Total with taxes and fees
Waterfront cabin w/ workspace & BBQ grill
A rustic cabin interior with a leather sofa, wooden beams, and mounted animal heads.

16. Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (86 reviews)
"The best, peaceful, fun, ATV wheeling, target practice, grilling, great kitchen supplies and plenty of space for the family Would stay again"
United States
Lisa G.
$288 nightly
The price is $320
Aug 26 - Aug 27
Total with taxes and fees
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

17. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (7 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
$206 nightly
The price is $218
Aug 25 - Aug 26
Total with taxes and fees
The Suite On Smallwood
A rustic log cabin with a green roof, a porch with outdoor seating, and a sign indicating an office entrance.

18. 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.
$168 nightly
The price is $169
Aug 24 - Aug 25
Total with taxes and fees
Private cabin with two full beds. ADA accessible.
A modern house with a hot tub, deck, and a fire pit.

19. Hart's Overlook | Hot Tub, Stunning Mtn Views + Private Pond!

Hart's Overlook | Hot Tub, Stunning Mtn Views + Private Pond!
Augusta
9.8 out of 10, Exceptional, (23 reviews)
"Beautiful place, very clean and cozy"
United States
wade p.
$341 nightly
The price is $380
Aug 24 - Aug 25
Total with taxes and fees
Hart's Overlook | Hot Tub, Stunning Mtn Views + Private Pond!
A wooden cabin interior with a dining area, a sofa, and a balcony with a view of the mountains.

20. 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.
$291 nightly
The price is $313
Aug 27 - Aug 28
Total with taxes and fees
3BR cabin w/ scenic deck and pet-friendly
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

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

8/10 Good
"Very nice casino and resort...helpful staff..will stay aging in near future."
todd 1-night trip
Posted less than an hour ago
Rocky Gap Casino & Resort

Find out more about Oldtown

Everything you need to know about Oldtown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oldtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oldtown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oldtown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $151 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oldtown rentals

At Expedia, we put the best Oldtown vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Oldtown?

Yes, we have vacation rentals close to well known sights in Oldtown, or you can choose a more secluded option if you're looking for a relaxing stay. Oldtown is known for its parks.

What's the top vacation rental that Oldtown has to offer?

Cannon Cliffside River Retreat- FREE WIFI: This vacation home near Oldtown is located on a river and has a fireplace, a selection of games, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a 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 larger area.

What’s a vacation rental in Oldtown like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Oldtown. Vacation rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family trips.