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Oldtown Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (37 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
$201 nightly
The price is $213
Nov 2 - Nov 3
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, (20 reviews)
"Very clean and cozy cabins!"
United States
Abraham
$129 nightly
The price is $146
Oct 17 - Oct 18
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, (124 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.
$294 nightly
The price is $332
Nov 3 - Nov 4
Total with taxes and fees
Secluded, romantic cabin with hot tub on 12 acres of woodland.
A grassy field with a wooden fence and trees in the background.

4. 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, (19 reviews)
"The tiny house was very clean, we were able to message the host easily."
United States
Brenda B.
$168 nightly
The price is $187
Oct 18 - Oct 19
Total with taxes and fees
Charming Cottage on 15 Acre Farm near Romney, WV
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, (53 reviews)
"Great stay"
United States
Michael R.
$181 nightly
The price is $192
Oct 15 - Oct 16
Total with taxes and fees
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, (45 reviews)
"Lovely place everyone enjoyed staying here, very clean and excellent location"
United States
William R.
$333 nightly
The price is $335
Oct 20 - Oct 21
Total with taxes and fees
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

7. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (10 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
$193 nightly
The price is $205
Oct 19 - Oct 20
Total with taxes and fees
The Suite On Smallwood
A bedroom with a bed, two windows, and a radiator.

8. Mountain View Condo - Steps to C&O Trail

Mountain View Condo - Steps to C&O Trail
Cumberland
Mountain View Condo - Steps to C&O Trail
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, (64 reviews)
"Host was very polite and helpful!"
United States
Quintin
$165 nightly
The price is $175
Oct 18 - Oct 19
Total with taxes and fees
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
Exterior

10. Serene Riverfront Cabin Haven near South Branch Potomac River in West Virginia

Serene Riverfront Cabin Haven near South Branch Potomac River in West Virginia
Springfield
$288 nightly
The price is $320
Oct 14 - Oct 15
Total with taxes and fees
Serene Riverfront Cabin Haven near South Branch Potomac River in West Virginia
A dining area with a wooden table, chairs, and a view of trees through the window.

11. Lustrous Lakefront Cabin Oasis near Lake Ferndale in West Virginia

Lustrous Lakefront Cabin Oasis near Lake Ferndale in West Virginia
Springfield
$499 nightly
The price is $556
Oct 14 - Oct 15
Total with taxes and fees
Lustrous Lakefront Cabin Oasis near Lake Ferndale in West Virginia
A wooden staircase leading to a deck overlooking a forested valley with hills in the background.

12. Waterfront cabin w/ workspace & BBQ grill

Waterfront cabin w/ workspace & BBQ grill
Paw Paw
9.8 out of 10, Exceptional, (21 reviews)
"Very nice, clean and homey."
United States
Brenda D.
$421 nightly
The price is $457
Oct 14 - Oct 15
Total with taxes and fees
Waterfront cabin w/ workspace & BBQ grill
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

13. 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, (11 reviews)
"Easy walk into town and the train station."
United States
Kathy M.
$176 nightly
The price is $199
Oct 20 - Oct 21
Total with taxes and fees
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A deck with a white railing, a table, and a view of a forested landscape.

14. Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale

Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
La Vale
8.6 out of 10, Excellent, (7 reviews)
"The host was very responsive and accessible. The house is freshly updated and uncluttered. The beds and pillows are comfortable. The view is lovely. The showers are small but manageable and there is no washing machine or dryer at this property. Overall it is a nice place and met our need for sleeping and making breakfast. We will very likely stay here again when we are in the area visiting family."
United States
TRINA P.
$203 nightly
The price is $215
Oct 15 - Oct 16
Total with taxes and fees
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A cabin with a deck, surrounded by trees and a fire pit.

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.
$267 nightly
The price is $287
Oct 22 - Oct 23
Total with taxes and fees
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, (18 reviews)
"Lovely place! "
United States
Courtney N.
$172 nightly
The price is $194
Oct 14 - Oct 15
Total with taxes and fees
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
A two-story building with a green exterior, a black front door, and a small balcony with a metal railing.

17. 5 minute walk to downtown. Cozy family sized home with everything you need.

5 minute walk to downtown. Cozy family sized home with everything you need.
Frostburg
9.4 out of 10, Exceptional, (34 reviews)
"Lovely place, had all we needed for a comfortable stay. Thanks!"
United States
Molly M.
$209 nightly
The price is $236
Oct 14 - Oct 15
Total with taxes and fees
5 minute walk to downtown. Cozy family sized home with everything you need.
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.
$157 nightly
The price is $158
Oct 14 - Oct 15
Total with taxes and fees
Private cabin with two full beds. ADA accessible.
A high-ceilinged room with large windows, a wooden interior, a sofa, a coffee table, and a fireplace.

19. 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.
$377 nightly
The price is $409
Oct 20 - Oct 21
Total with taxes and fees
Upscale w Fireplace, Fire Pit, Games in Gated Comm
A small attic bedroom with a sloped ceiling, a single bed, and a window.

20. Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
9.4 out of 10, Exceptional, (14 reviews)
"Always a great stay. Peaceful and plenty to explore. We cant wait to come back!"
United States
Anthony A.
$176 nightly
The price is $196
Oct 15 - Oct 16
Total with taxes and fees
Primitive Cozy Tiny Cabin with Starlink internet
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

10/10 Excellent
"Clean room and grounds, friendly and professional staff."
Cheryl 2-night trip
Posted 3 hours 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 $146 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?

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi: This vacation home near Oldtown is equipped with a barbecue grill, 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 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.