Book Holiday Homes in Oldtown

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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
Stay at this vacation home in Great Cacapon. Enjoy a garden, a pool table, and patios. Popular attractions Frog Valley Artisans, LTD and Prospect Peak are located ...
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
Book a stay at this family-friendly vacation home in Berkeley Springs. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Colonial Springs ...
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
Book a stay at this family-friendly vacation home in Springfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attraction Potomac Eagle Scenic ...
Run away to the mountains of WV! Peaceful country home is waiting for you!
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$236 per night from 7 Apr to 8 Apr
NZ$236
includes taxes & fees
7 Apr - 8 Apr
Stay at this vacation home in Cumberland. Enjoy air conditioning. Popular attractions Tri-State Zoological Park and Downtown Cumberland Historic District are ...
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Oldtown Guesthouse

Oldtown Guesthouse

Oldtown
The price is NZ$320 per night from 14 Apr to 15 Apr
NZ$320
includes taxes & fees
14 Apr - 15 Apr
Stay at this vacation home in Oldtown. Enjoy free WiFi, patios, and an in-room coffeemaker.
Oldtown Guesthouse
Serene Springfield Retreat on 6 Acres w/ Hot Tub!

Serene Springfield Retreat on 6 Acres w/ Hot Tub!

Springfield
Stay at this vacation home in Springfield. Enjoy a garden, patios, and cable/satellite TV service.
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
Book a stay at this family-friendly vacation home in Great Cacapon. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Cacapon Resort ...
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!
Cannon Cliffside River Retreat-  FREE WIFI

Cannon Cliffside River Retreat- FREE WIFI

Springfield
Stay at this vacation home in Springfield. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attraction Potomac Eagle Scenic Railroad is ...
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
The price is NZ$430 per night from 5 Apr to 6 Apr
NZ$430
includes taxes & fees
5 Apr - 6 Apr
Book a stay at this family-friendly vacation home in Cumberland. Enjoy free WiFi, a garden, and patios. Popular attractions F. Brooke Whiting House and Museum ...
Full home near C&O & Polar Express! Perfect for bikers or families!
Don't see what you're looking for?
See all available properties in Oldtown
View all properties
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
156 Holiday Homes
Lowest Price
NZ$152
Highest Price
NZ$625
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 NZ$239 per night from 10 Apr to 11 Apr
NZ$239
includes taxes & fees
10 Apr - 11 Apr
Stay at this 3-star spa hotel in Cumberland. Enjoy free parking, an outdoor pool, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
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 NZ$625 per night from 24 Apr to 25 Apr
NZ$625
includes taxes & fees
24 Apr - 25 Apr
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Frog Valley Artisans, LTD and Colonial Springs ...
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 NZ$168 per night from 13 Apr to 14 Apr
NZ$168
includes taxes & fees
13 Apr - 14 Apr
Book a stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
Best Western Braddock Inn
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$152 per night from 20 Apr to 21 Apr
NZ$152
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Ramada by Wyndham Cumberland Downtown
Don't see what you're looking for?
See all available properties in Oldtown
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.