Oldtown Holiday Rentals from NZ$266: Search Short-Term Rentals

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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

Stephanie R.

includes taxes & fees

9 Nov - 10 Nov

A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

2. The Suite On Smallwood

Cumberland

Joseph S.

includes taxes & fees

6 Nov - 7 Nov

A garden with a variety of flowers and plants, a wooden structure, and a white fence.

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

Cumberland

WILSON

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a dining area, large windows, and a stone fireplace.

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

Cumberland

John V.

includes taxes & fees

9 Nov - 10 Nov

A grassy field with a wooden fence and trees in the background.

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

Romney

Hileri G.

includes taxes & fees

9 Nov - 10 Nov

A covered patio with a table and chairs, a hanging basket, and a satellite dish.

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

Cumberland

Quintin

includes taxes & fees

5 Nov - 6 Nov

A bedroom with a skylight, a bed, two windows, and a radiator.

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

Cumberland

includes taxes & fees

5 Nov - 6 Nov

A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

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

Cumberland

Kathy M.

includes taxes & fees

5 Nov - 6 Nov

A small attic bedroom with a sloped ceiling, a single bed, and a window.

9. Primitive Cozy Tiny Cabin with Starlink internet

Great Cacapon

Anthony A.

includes taxes & fees

5 Nov - 6 Nov

A rustic cabin with a porch and outdoor seating area.

10. Waterfront cabin w/ workspace & BBQ grill

Paw Paw

Lisa C.

includes taxes & fees

16 Nov - 17 Nov

A blue door with the number 137, a wreath, and a mailbox.

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

Cumberland

Courtney N.

includes taxes & fees

5 Nov - 6 Nov

An outdoor wooden deck with seating, a large tree, and a glass-enclosed room with a bench.

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

Springfield

William R.

includes taxes & fees

8 Nov - 9 Nov

A wooden cabin with a porch, a green door, and a window.

13. 1/2 of a double cabin with one king sized bed (sleeps 2)

Flintstone

"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...

LaRon G.

includes taxes & fees

5 Nov - 6 Nov

A single-story house with a covered porch and a chimney, surrounded by trees and a view of a forested hill.

14. Private, clean mountain home near Rocky Gap!

Cumberland

Alisa S.

includes taxes & fees

17 Nov - 18 Nov

A two-story building with a green exterior, a black front door, and a small balcony with a metal railing.

15. 5 minute walk to downtown. Cozy family sized home with everything you need.

Frostburg

Sofia

includes taxes & fees

6 Nov - 7 Nov

A high-ceilinged room with large windows, a wooden interior, a sofa, a coffee table, and a fireplace.

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

Paw Paw

Jella S.

includes taxes & fees

12 Nov - 13 Nov

A wooden deck with a hot tub, a table, and benches.

17. Peaceful and relaxing three bedroom home with hot tub, right beside I-68

La Vale

includes taxes & fees

9 Nov - 10 Nov

A deck with a white railing, a table, and a view of a forested landscape.

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

La Vale

"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."

TRINA P.

includes taxes & fees

9 Nov - 10 Nov

A wooden cabin with a dining area, seating, and a view of the landscape.

19. Mountain chalet w/ hot tub & private balcony

Augusta

Leigh Ann P.

includes taxes & fees

30 Nov - 1 Dec

20. Rustic Oasis for the Family - 6 min walk to Downtown

Cumberland

Sharon D.

includes taxes & fees

11 Nov - 12 Nov

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Find holiday rentals that suit your style

Top Oldtown Hotel Reviews

An indoor swimming pool with lounge chairs and a hot tub.

Fairfield Inn & Suites by Marriott Cumberland

Cumberland

8/10 Good

Geoffrey

Rocky Gap Casino & Resort

Cumberland

10/10 Excellent

John

A spacious living room with a brown leather sofa, a green patterned rug, a stone fireplace, and a large window with a view of a building.

Clarysville Motel

Frostburg

8/10 Good

This hotel worked out great for a one night stay for the low price I paid. It isn't really wheelchair accessible as there are lips on the steep ramp getting up to the rooms and each entrance to the rooms have a lip. Owner did every thing he could to make it usable for me, take door off bathroom, but to tight to use the toilet. I could get to the sink to wash hands but not a chance of getting a shower. Luckily McDonalds was 2 minutes down the street so I used their toilet and Save Alot and...

Holly

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 favorite 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 depends 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 NZ$266 per night. Entering your travel dates in the search wizard you might find 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?

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.

Oldtown Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oldtown holiday rentals

1. Oldtown Guesthouse

2. The Suite On Smallwood

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

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

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

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

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

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

9. Primitive Cozy Tiny Cabin with Starlink internet

10. Waterfront cabin w/ workspace & BBQ grill

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

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

13. 1/2 of a double cabin with one king sized bed (sleeps 2)

14. Private, clean mountain home near Rocky Gap!

15. 5 minute walk to downtown. Cozy family sized home with everything you need.

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

17. Peaceful and relaxing three bedroom home with hot tub, right beside I-68

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

19. Mountain chalet w/ hot tub & private balcony

20. Rustic Oasis for the Family - 6 min walk to Downtown

Find holiday rentals that suit your style

Top Oldtown Hotel Reviews

Fairfield Inn & Suites by Marriott Cumberland

8/10 Good

Find out more about Oldtown

Oldtown holiday rentals: An excellent choice for every season

How to find incredible deals on Oldtown rentals

Frequently Asked Questions

Can I find holiday rentals in Oldtown?

What are some of the best holiday rentals that Oldtown has to offer?

What’s there to see and do in Oldtown?

What’s a holiday rental in Oldtown like?