Woodland Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Woodland vacation rentals

Pool
BIG D's POND & North Branch of the Potomac river Camping.

Camping in Cumberland

BIG D's POND & North Branch of the Potomac river Camping.
10.0 out of 10, Exceptional, (3)
"Big D'S Pond is beautiful and the owner, is very kind and helpful. We had an amazing time!"
United States
Mary G.
The price is ￥9,695
￥17,724 total
includes taxes & fees
Dec 26 - Dec 27
BIG D's POND & North Branch of the Potomac river Camping.
Fridge, microwave, oven, stovetop
Oldtown Guesthouse

Vacation Home in Oldtown

Oldtown Guesthouse
10.0 out of 10, Exceptional, (28)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
United States
Elizabeth
The price is ￥15,612
￥28,133 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Oldtown Guesthouse
Interior
Loft two story with first floor workout room, WIFI, complete cottage to yourself

Cottage in Grantsville

Loft two story with first floor workout room, WIFI, complete cottage to yourself
9.8 out of 10, Exceptional, (37)
"The clean and comfortable looking cabins "
United States
Torrance
The price is ￥18,969
￥31,691 total
includes taxes & fees
Dec 25 - Dec 26
Loft two story with first floor workout room, WIFI, complete cottage to yourself
4 bedrooms, WiFi, bed sheets
Right off the bike trail.

Vacation Home in Meyersdale

Right off the bike trail.
9.6 out of 10, Exceptional, (98)
"What a wonderful, homely spot! If only those walls could tell their stories. "
United States
Anthony
The price is ￥15,612
￥21,506 total
includes taxes & fees
Dec 26 - Dec 27
Right off the bike trail.
Property grounds
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Vacation Home in Cumberland

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
9.8 out of 10, Exceptional, (33)
"We had a nice relaxing stay at this lovely cottage. It was convenient to downtown and very clean."
United States
Reni J.
The price is ￥16,861
￥27,802 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Interior
Full home near C&O! Perfect for bikers or families!

Vacation Home in Cumberland

Full home near C&O! Perfect for bikers or families!
9.6 out of 10, Exceptional, (21)
"Overall our stay was fine."
United States
Steve J.
The price is ￥21,076
￥35,580 total
includes taxes & fees
Dec 27 - Dec 28
Full home near C&O! Perfect for bikers or families!
Interior
Secluded, romantic cabin with hot tub on 12 acres of woodland.

Cabin in Cumberland

Secluded, romantic cabin with hot tub on 12 acres of woodland.
10.0 out of 10, Exceptional, (105)
"Very clean, nicely appointed, good quality."
United States
Yisrael D.
The price is ￥30,443
￥51,900 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Interior
Private Home in Garrett County, surrounded by trees, fields and farmland.

Cottage in Grantsville

Private Home in Garrett County, surrounded by trees, fields and farmland.
10.0 out of 10, Exceptional, (42)
"We had a very nice stay. Very comfortable and inviting a home away from home vibe. "
United States
Carol R.
The price is ￥24,823
￥44,350 total
includes taxes & fees
Dec 25 - Dec 26
Private Home in Garrett County, surrounded by trees, fields and farmland.
2 bedrooms, free WiFi, bed sheets
A Cozy Tiny house by the GAP Trail & view of the Sand Patch grade.

Cabin in Meyersdale

A Cozy Tiny house by the GAP Trail & view of the Sand Patch grade.
10.0 out of 10, Exceptional, (10)
"This was a very nice place to stay and the host was very accommodating to a last minute booking! "
United States
Haley C.
The price is ￥37,313
￥48,942 total
includes taxes & fees
Jan 5 - Jan 6, 2026
A Cozy Tiny house by the GAP Trail & view of the Sand Patch grade.
Exterior detail
5 minute walk to downtown. Cozy family sized home with everything you need.

Apartment in Frostburg

5 minute walk to downtown. Cozy family sized home with everything you need.
9.4 out of 10, Exceptional, (27)
"Cozy and charming. Great location. Would certainly book again. "
United States
Dennis F.
The price is ￥17,954
￥35,842 total
includes taxes & fees
Dec 25 - Dec 26
5 minute walk to downtown. Cozy family sized home with everything you need.
Dining
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.

Cottage in Grantsville

Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
2.0 star property
The price is ￥23,106
￥27,802 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
Interior
Historic Mountain Retreat: Breathtaking views, pet friendly, trampoline/playroom

Vacation Home in Cumberland

Historic Mountain Retreat: Breathtaking views, pet friendly, trampoline/playroom
9.0 out of 10, Wonderful, (2)
"We had a great stay, it ended up being at a different property than we booked but it was still an enjoyable stay. Communication was excellent and I would recommend. Thank you"
United States
Tina B.
The price is ￥17,954
￥56,100 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Historic Mountain Retreat: Breathtaking views, pet friendly, trampoline/playroom
Terrace/patio
Historic Farm, Near Lake, 10 Acres, Newly Renovated

Vacation Home in Swanton

Historic Farm, Near Lake, 10 Acres, Newly Renovated
9.8 out of 10, Exceptional, (10)
"The Historic Farm property was beautiful! Our family enjoyed fishing at the pond and biking in and around the property. We hiked and swam in the nearby State Parks. The bedrooms were spacious and the king sized beds comfortable. It was great to have meals with the whole family around the large dining room table. The ice machine in the cozy kitchen was an added bonus."
United States
Cheryl W.
The price is ￥257,598
￥365,761 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Historic Farm, Near Lake, 10 Acres, Newly Renovated
Interior
Perfect 4 Holidays: Mountain view Grand 6BR 3BA LaVale Home, 15 min to Rocky Gap

Vacation Home in La Vale

Perfect 4 Holidays: Mountain view Grand 6BR 3BA LaVale Home, 15 min to Rocky Gap
9.6 out of 10, Exceptional, (7)
"Absolutely wonderful! Historic home with lots of charm in a great location. The house was very clean and well appointed. The owner was great to deal with and they even had extra tissues sent from Amazon knowing we were in town for a funeral! Will definitely stay here again! "
United States
Theresa F.
The price is ￥46,680
￥93,004 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Perfect 4 Holidays: Mountain view Grand 6BR 3BA LaVale Home, 15 min to Rocky Gap
Fridge, microwave, oven, stovetop
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!

Apartment in Cumberland

Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
10.0 out of 10, Exceptional, (7)
"The property was exactly as described. The location was perfect for walking around safely to restaurants, and the communication with the property owner was excellent!"
United States
Evelyn W.
The price is ￥22,973
￥27,661 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
Smart TV, books
Top of the GAP guesthouse on the Eastern Continental Divide.

Vacation Home in Meyersdale

Top of the GAP guesthouse on the Eastern Continental Divide.
10.0 out of 10, Exceptional, (1)
"The house was very cozy, clean and had great amenities! "
United States
Cindy I.
The price is ￥30,600
￥38,600 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Top of the GAP guesthouse on the Eastern Continental Divide.
View from property
Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake

Cabin in Accident

Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
10.0 out of 10, Exceptional, (217)
"Family friendly "
United States
Henok
The price is ￥25,994
￥66,446 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
Business center
Knit Inn..

Vacation Home in Frostburg

Knit Inn..
9.6 out of 10, Exceptional, (8)
"We loved our stay! Jennifer was very great and we loved the food and town of Frostburg "
United States
Anonymous traveler
The price is ￥62,448
￥94,493 total
includes taxes & fees
Dec 25 - Dec 26
Knit Inn..
TV
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!

Apartment in Cumberland

Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
9.8 out of 10, Exceptional, (13)
"Cozy and great location for getting to the bike trail and around town."
United States
havala m.
The price is ￥24,659
￥29,449 total
includes taxes & fees
Dec 25 - Dec 26
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Property grounds
Private Room 2 & Bath, 10 Acres, Lake Access

Vacation Home in Swanton

Private Room 2 & Bath, 10 Acres, Lake Access
The price is ￥34,346
￥77,991 total
includes taxes & fees
Dec 25 - Dec 26
Private Room 2 & Bath, 10 Acres, Lake Access
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 Woodland Hotel Reviews

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

10/10 Excellent
"Everything was as expected."
Dontcho 2-night trip
Posted 2 days ago
Rocky Gap Casino & Resort

Find out more about Woodland

Search for holiday rentals in Woodland on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodland using one of the methods below:

  • View our selection of featured holiday rentals in Woodland
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Look no further and take a look at our great range of rental properties in Woodland!

Frequently asked questions

Can I find a vacation rental in Woodland?

Yes, we have vacation rentals close to popular attractions in Woodland, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Woodland?

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym): This vacation home rental near Woodland is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Woodland?

While exploring the area, visit family-friendly sights like Tri-State Zoological Park, or get outside and enjoy nature at Savage River. In the larger area, you’ll find Noah's Ark and Frostburg State University.

What are vacation rentals like in Woodland?

Vacation rentals are privately owned properties you can book for several days or longer in Woodland. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.