Book Holiday Homes in Oldtown

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Featured Holiday Homes in Oldtown

Charming mountaintop cabin with pool table and breathtaking views

Charming mountaintop cabin with pool table and breathtaking views

Great Cacapon
Located in Great Cacapon, this vacation home is on a river, a 3-minute drive from Lost River and 8 minutes from Cacapon Resort State Park.
Charming mountaintop cabin with pool table and breathtaking views
Beautiful Log Chalet/Cabin with Hot Tub

Beautiful Log Chalet/Cabin with Hot Tub

Berkeley Springs
Located in Berkeley Springs, this vacation home is in the mountains, within a 10-minute drive of Cacapon Resort State Park and Colonial Springs Spa.
Beautiful Log Chalet/Cabin with Hot Tub
Run away to the mountains of WV! Peaceful country home is waiting for you!

Run away to the mountains of WV! Peaceful country home is waiting for you!

Springfield
Located in Springfield, this vacation home is on the waterfront, within a 15-minute drive of Potomac Eagle Scenic Railroad and Literary Hall.
Run away to the mountains of WV! Peaceful country home is waiting for you!
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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
The price is AU$309 per night from 1 May to 2 May
AU$309
includes taxes & fees
1 May - 2 May
With a stay at this vacation home in Cumberland, you'll be within a 5-minute drive of Tri-State Zoological Park and UPMC Western Maryland.
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Oldtown Guesthouse

Oldtown Guesthouse

Oldtown
The price is AU$298 per night from 6 Apr to 7 Apr
AU$298
includes taxes & fees
6 Apr - 7 Apr
Located in Oldtown, this vacation home is within a 5-minute drive of Chesapeake and Ohio Canal and Chesapeake and Ohio Canal National Historic Park.
Oldtown Guesthouse
Serene Springfield Retreat on 6 Acres w/ Hot Tub!

Serene Springfield Retreat on 6 Acres w/ Hot Tub!

Springfield
With a stay at this vacation home in Springfield, you'll be 11.5 mi (18.5 km) from Potomac Eagle Scenic Railroad and 12.7 mi (20.5 km) from Chesapeake and Ohio ...
Serene Springfield Retreat on 6 Acres w/ Hot Tub!
Breathtaking!  5 Acre Private Riverfront Cabin in the Mountains!

Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

Great Cacapon
Located in Great Cacapon, this vacation home is on the waterfront, a 1-minute drive from Lost River and 6 minutes from Sideling Hill Wildlife Management ...
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!
Cannon Cliffside River Retreat-  FREE WIFI

Cannon Cliffside River Retreat- FREE WIFI

Springfield
Located in Springfield, this vacation home is on a river, within a 15-minute drive of Potomac Eagle Scenic Railroad and Literary Hall.
Cannon Cliffside River Retreat- FREE WIFI
Full home near C&O & Polar Express! Perfect for bikers or families!

Full home near C&O & Polar Express! Perfect for bikers or families!

Cumberland
With a stay at this vacation home in Cumberland, you'll be within a 10-minute walk of F. Brooke Whiting House and Museum and Gordon Roberts House.
Full home near C&O & Polar Express! Perfect for bikers or families!
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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.

Oldtown Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oldtown vacation homes are the perfect way for you to wing it.

Holiday houses in Oldtown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oldtown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oldtown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oldtown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oldtown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oldtown Holiday Homes essential information

Accommodation
155 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$572
Popular accommodation
Charming mountaintop cabin with pool table and breathtaking views, Beautiful Log Chalet/Cabin with Hot Tub, Run away to the mountains of WV! Peaceful country home is waiting for you! , Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi, Oldtown Guesthouse, Serene Springfield Retreat on 6 Acres w/ Hot Tub!, Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains! , Cannon Cliffside River Retreat- FREE WIFI, Full home near C&O & Polar Express! Perfect for bikers or families!

Top trending hotels in Oldtown

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 13 Apr to 14 Apr
AU$221
includes taxes & fees
13 Apr - 14 Apr
When you a stay at Rocky Gap Casino & Resort in Cumberland, you'll be next to a golf course, just steps from Rocky Gap State Park and Rocky Gap Casino and Golf ...
Rocky Gap Casino & Resort
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
The price is AU$572 per night from 24 Apr to 25 Apr
AU$572
includes taxes & fees
24 Apr - 25 Apr
When you stay at this cabin in Berkeley Springs, you'll be in the mountains, within a 5-minute drive of Cacapon Resort State Park and Frog Valley Artisans, ...
Dreamtime - Modern A-frame Cabin w/ Hot tub
Best Western Braddock Inn

Best Western Braddock Inn

2.5 out of 5
1268 National Hwy, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 9 Apr to 10 Apr
AU$140
includes taxes & fees
9 Apr - 10 Apr
Located in Cumberland, Best Western Braddock Inn is within a 5-minute drive of La Vale Tollgate House and Country Club Mall.
Best Western Braddock Inn
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Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 9 Apr to 10 Apr
AU$140
includes taxes & fees
9 Apr - 10 Apr
A stay at Ramada by Wyndham Cumberland Downtown places you in the heart of Cumberland, steps from Downtown Cumberland Historic District and 4 minutes by foot ...
Ramada by Wyndham Cumberland Downtown
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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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^Subject to availability and chosen travel dates.