Photo by Kayla Berry

Search Vacation Homes in Oldtown

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 156 Vacation Homes in Oldtown with updated reviews, rates, and availability.

Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Outdoor dining

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (199)
"We had a great stay. The hosts were responsive. The cabin was beautiful with great views and a perfect getaway. Definitely would stay again."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Beautiful Log Chalet/Cabin with Hot Tub
Smart TV, fireplace, DVD player, computer

Beautiful Log Chalet/Cabin with Hot Tub

10.0 out of 10, Exceptional, (65)
"Beautiful Cabin!"
Beautiful Log Chalet/Cabin with Hot Tub
Run away to the mountains of WV! Peaceful country home is waiting for you!
Miscellaneous

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

10.0 out of 10, Exceptional, (43)
"You can really tell the house is cared for. It feels like a home. It had everything you could need. They have a well stocked kitchen and even supply snacks. The beds were very comfortable. The yard is huge with a stream behind it with a Great fire pit. I do recommend this property and will definitely go back"
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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (7)
"Nice clean well kept cottage. "
The price is AED 441
AED 709 total
includes taxes & fees
12 May - 13 May
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Oldtown Guesthouse
Fridge, microwave, oven, stovetop

Oldtown Guesthouse

10.0 out of 10, Exceptional, (21)
"Great place to stay. Location was great for our visits to the Western Maryland Scenic Railroad and the Potomac Eagle Scenic Railroad. Host prepared a welcoming, well appointed home for our stay. Very clean and well maintained."
The price is AED 397
AED 693 total
includes taxes & fees
8 May - 9 May
Oldtown Guesthouse
Serene Springfield Retreat on 6 Acres w/ Hot Tub!
Terrace/patio

Serene Springfield Retreat on 6 Acres w/ Hot Tub!

10.0 out of 10, Exceptional, (9)
"We loved the property"
Serene Springfield Retreat on 6 Acres w/ Hot Tub!
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!
Property grounds

Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

9.8 out of 10, Exceptional, (50)
"The property was beautiful. Our host were very accommodating and easy to get ahold of. This house had a lot of space for a bigger group. We all enjoyed our stay very much."
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!
Cannon Cliffside River Retreat- FREE WIFI
Fridge, microwave, oven, stovetop

Cannon Cliffside River Retreat- FREE WIFI

10.0 out of 10, Exceptional, (23)
"Wonderful home with beautiful surroundings "
Cannon Cliffside River Retreat- FREE WIFI
Full home near C&O! Perfect for bikers or families!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (10)
"We were very impressed with this location. It is in a beautiful section of town and close to town. It was everything we could ask for for our family of 5."
The price is AED 551
AED 923 total
includes taxes & fees
8 May - 9 May
Full home near C&O! Perfect for bikers or families!
Historic William Smith House - Pets | Grill | Creekside | Wifi | Deck | Fire Pit
Fridge, microwave, oven, stovetop

Historic William Smith House - Pets | Grill | Creekside | Wifi | Deck | Fire Pit

10.0 out of 10, Exceptional, (3)
"We enjoyed the home and appreciated efforts by property managers to make our stay more comfortable. "
Historic William Smith House - Pets | Grill | Creekside | Wifi | Deck | Fire Pit
Serendipity - Hot Tub | Pets | Fire Pit | Pool Access | Grill | Wifi | Deck
Pool

Serendipity - Hot Tub | Pets | Fire Pit | Pool Access | Grill | Wifi | Deck

9.4 out of 10, Exceptional, (51)
"Great location and plenty of sleeping areas! Loved the hot tub!"
Serendipity - Hot Tub | Pets | Fire Pit | Pool Access | Grill | Wifi | Deck
Awesome New Property/ CANAL RIVER RETREAT
Lake

Awesome New Property/ CANAL RIVER RETREAT

9.8 out of 10, Exceptional, (107)
"As always, we loved sharing our Thanksgiving holiday with family at this lovely house and home. The location along the Potomac River and C&O Canal towpath is fabulous, so close to town yet our own little world. The space is perfect for a large gathering, plenty of room for tables for the meal and for games afterward. Thanks for everything. "
Awesome New Property/ CANAL RIVER RETREAT
Emerald in Berkeley Springs, WV
Terrace/patio

Emerald in Berkeley Springs, WV

10.0 out of 10, Exceptional, (27)
"Very secluded and quiet, spotless, great service when we had questions! Highly recommend!"
Emerald in Berkeley Springs, WV
Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded
Terrace/patio

Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded

2.0 star property
10.0 out of 10, Exceptional, (8)
"I booked this place for a weekend getaway with family. The location was great, isolated enough, but close to Berkeley Spring and some nice trails. We enjoyed the amenities, view and the well stocked kitchen. "
Trailblazer - hot tub, trail, game room, pets, wifi, fire pit, view, secluded
Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.
Smart TV, fireplace, DVD player, foosball

Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.

10.0 out of 10, Exceptional, (63)
"Beautiful house and property with all kind of fun toys in the basement. We enjoyed watching the birds in the newly filled feeders from the comfortable seating areas. Beds were super comfy as well! Our stay was cut short due to an incoming snow storm but the owners were very understanding and worked with us on that. We would love to come back when it’s warmer and can enjoy the property more."
Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.
Little cute house close to C&O canal
Smart TV

Little cute house close to C&O canal

8.6 out of 10, Excellent, (8)
"I felt very cozy and comfortable in this small home, at the top of the hill (great views). Everything was arranged just right. Communication with the host was very easy. I would happily return. Beth"
The price is AED 367
AED 662 total
includes taxes & fees
8 May - 9 May
Little cute house close to C&O canal
Renovated Farmhouse located near the C and O Canal
Exterior

Renovated Farmhouse located near the C and O Canal

9.0 out of 10, Wonderful, (8)
"We had a great stay at the house."
The price is AED 661
AED 946 total
includes taxes & fees
8 May - 9 May
Renovated Farmhouse located near the C and O Canal
✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟
Outdoor dining

✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

10.0 out of 10, Exceptional, (41)
"Lovely home, outstanding view and all the amenities!! Wonderful touches that made the stay so comfortable- it was a perfect spot for our family gathering!"
✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟
Cozy Appalachian Getaway: 5 Mi to Prospect Peak!
Fridge, microwave, stovetop, dishwasher

Cozy Appalachian Getaway: 5 Mi to Prospect Peak!

9.6 out of 10, Exceptional, (7)
"Woodsy and private."
Cozy Appalachian Getaway: 5 Mi to Prospect Peak!
Knit Inn..
4 bedrooms, WiFi, bed sheets

Knit Inn..

9.4 out of 10, Exceptional, (3)
"House was perfect for our group of 10 and convenient to restaurants and historical places. Host was very helpful in working thru some small issues we needed for the night. Recommend for quick getaway destination."
The price is AED 1,543
AED 2,313 total
includes taxes & fees
8 May - 9 May
Knit Inn..
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.
Don't see what you're looking for?
See all available properties in Oldtown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Oldtown

Oldtown Guesthouse
Fridge, microwave, oven, stovetop

Oldtown Guesthouse

10.0 out of 10, Exceptional, (21)
"Great place to stay. Location was great for our visits to the Western Maryland Scenic Railroad and the Potomac Eagle Scenic Railroad. Host prepared a welcoming, well appointed home for our stay. Very clean and well maintained."
The price is AED 397
AED 693 total
includes taxes & fees
8 May - 9 May
Oldtown Guesthouse
Loft Cabin w, Hot Tub, Fire Pit, Huge Deck & WiFi!
Fridge, microwave, oven, stovetop

Loft Cabin w, Hot Tub, Fire Pit, Huge Deck & WiFi!

9.0 out of 10, Wonderful, (18)
"This adorable cabin was perfect for our couples weekend away! Very clean, stocked with essentials (linens, cookware, utensils, etc) and spacious. The hot tub and fire pit were perfect to help unplug and relax. Tony was a phenomenal host, was quick to respond to any questions/concerns and made sure every part of our stay was satisfactory. Would definitely return or stay at other properties from this host. "
The price is AED 541
AED 647 total
includes taxes & fees
8 May - 9 May
Loft Cabin w, Hot Tub, Fire Pit, Huge Deck & WiFi!
Hidden Gem in the woods with hot tub
Property grounds

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (76)
"Beautiful location and great little cabin "
Hidden Gem in the woods with hot tub
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.