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Woodland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Woodland vacation rentals

A sunroom with large windows, a ceiling fan, and a table with chairs.

1. Mid Century-Modern Retreat Great Allegheny Passage

Mid Century-Modern Retreat Great Allegheny Passage
Cresaptown, MD
$263 nightly
The price is $279
Nov 8 - Nov 9
Total with taxes and fees
Mid Century-Modern Retreat Great Allegheny Passage
A bedroom with a large bed, wooden headboard, two bedside tables with lamps, a floral-patterned rug, and a window with curtains.

2. Right off the bike trail.

Right off the bike trail.
Meyersdale
9.6 out of 10, Exceptional, (128 reviews)
"Plenty of space (4 standalone bedrooms), plus a full kitchen and handy laundry machine & dryer!! As the title says a short 300 ft directly off the GAP. House was cosy warm too!!"
United States
Sholto
$109 nightly
The price is $121
Nov 8 - Nov 9
Total with taxes and fees
Right off the bike trail.
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

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (57 reviews)
"comfortable cottage. In between most activity areas."
United States
WILSON
$173 nightly
The price is $183
Nov 6 - Nov 7
Total with taxes and fees
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A covered patio with a table and chairs, a hanging basket, and a satellite dish.

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

Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
Cumberland
10.0 out of 10, Exceptional, (66 reviews)
"Host was very polite and helpful!"
United States
Quintin
$157 nightly
The price is $166
Nov 6 - Nov 7
Total with taxes and fees
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

5. The Suite On Smallwood

The Suite On Smallwood
Cumberland
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful place at a great price within walking distance of downtown."
United States
Joseph S.
$183 nightly
The price is $194
Nov 6 - Nov 7
Total with taxes and fees
The Suite On Smallwood
A two-story building with a green exterior, a black front door, and a small balcony with a metal railing.

6. 5 minute walk to downtown. Cozy family sized home with everything you need.

5 minute walk to downtown. Cozy family sized home with everything you need.
Frostburg
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay when visiting Frostburg"
United States
Sofia
$200 nightly
The price is $227
Nov 6 - Nov 7
Total with taxes and fees
5 minute walk to downtown. Cozy family sized home with everything you need.
A modern interior with a dining area, kitchen, and a red-framed sliding door.

7. Mountain-View Condo w/ Patio & Free Parking

Mountain-View Condo w/ Patio & Free Parking
Cumberland
$207 nightly
The price is $216
Nov 8 - Nov 9
Total with taxes and fees
Mountain-View Condo w/ Patio & Free Parking
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!

Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
Cumberland
10.0 out of 10, Exceptional, (11 reviews)
"Easy walk into town and the train station."
United States
Kathy M.
$167 nightly
The price is $189
Nov 6 - Nov 7
Total with taxes and fees
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A serene pond with a wooden dock and chairs, surrounded by lush greenery and trees.

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

BIG D's POND & North Branch of the Potomac river Camping.
Cumberland
10.0 out of 10, Exceptional, (4 reviews)
"Big D'S Pond is beautiful and the owner, is very kind and helpful. We had an amazing time!"
United States
Mary G.
$117 nightly
The price is $124
Nov 6 - Nov 7
Total with taxes and fees
BIG D's POND & North Branch of the Potomac river Camping.
A blue door with the number 137, a wreath, and a mailbox.

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

Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Cumberland
9.8 out of 10, Exceptional, (19 reviews)
"Lovely place! "
United States
Courtney N.
$160 nightly
The price is $182
Nov 6 - Nov 7
Total with taxes and fees
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
A modern kitchen with a white island, black chairs, and a view of the outdoors.

11. Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.

Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
Grantsville
10.0 out of 10, Exceptional, (6 reviews)
"Great place to stay!! Very clean and extremely close to local attractions. "
United States
Mitchum
$221 nightly
The price is $234
Nov 8 - Nov 9
Total with taxes and fees
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
A wooden deck with a hot tub, a table, and benches.

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

Peaceful and relaxing three bedroom home with hot tub, right beside I-68
La Vale
$219 nightly
The price is $232
Nov 9 - Nov 10
Total with taxes and fees
Peaceful and relaxing three bedroom home with hot tub, right beside I-68
A wooden interior with a spiral staircase, a kitchen area, and a dining space.

13. Private Home in Garrett County, surrounded by trees, fields and farmland.

Private Home in Garrett County, surrounded by trees, fields and farmland.
Grantsville
10.0 out of 10, Exceptional, (62 reviews)
"We have stayed here 3 times and would highly recommend it. It is a great place for our family to be together."
United States
Carolin M.
$227 nightly
The price is $241
Nov 29 - Nov 30
Total with taxes and fees
Private Home in Garrett County, surrounded by trees, fields and farmland.
A kitchen with a central island, bar stools, a refrigerator, and a window with blinds.

14. Newly renovated 1905 house, within walking distance to all downtown attractions!

Newly renovated 1905 house, within walking distance to all downtown attractions!
Cumberland
10.0 out of 10, Exceptional, (2 reviews)
"The property, the price, the location, the host...all were perfect for or GAP bike trip!!!"
United States
Mark M.
$249 nightly
The price is $264
Nov 9 - Nov 10
Total with taxes and fees
Newly renovated 1905 house, within walking distance to all downtown attractions!
A deck with a white railing, a table, and a view of a forested landscape.

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

Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
La Vale
8.8 out of 10, Excellent, (10 reviews)
"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."
United States
TRINA P.
$194 nightly
The price is $206
Nov 9 - Nov 10
Total with taxes and fees
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A kitchen with white tiled backsplash, wooden shelves holding glassware, and a coffee maker on the counter.

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

Secluded, romantic cabin with hot tub on 12 acres of woodland.
Cumberland
10.0 out of 10, Exceptional, (127 reviews)
"Awesome home! Cabin was clean, comfortable, relaxing, everything we wanted. Add in a beautiful private deck with huge hot tub and an incredible bath tub with amazing shower, we could not have asked for more."
United States
John V.
$270 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Secluded, romantic cabin with hot tub on 12 acres of woodland.
A hot tub outside a building with a 'Welcome' sign, outdoor seating, and a view of the sky.

17. Tiny House in the Orchard; a Romantic Stay for two

Tiny House in the Orchard; a Romantic Stay for two
Swanton
$200 nightly
The price is $216
Nov 16 - Nov 17
Total with taxes and fees
Tiny House in the Orchard; a Romantic Stay for two
A cabin with a deck, a hot tub, and a view of the surrounding forest.

18. Romantic Riverside Getaway! Riverview Hot Tub!

Romantic Riverside Getaway! Riverview Hot Tub!
Grantsville
$354 nightly
The price is $382
Nov 17 - Nov 18
Total with taxes and fees
Romantic Riverside Getaway! Riverview Hot Tub!
A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

19. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (37 reviews)
"Wonderful property, comfy and perfect for a getaway. Definitely need to come back."
United States
Stephanie R.
$200 nightly
The price is $212
Nov 9 - Nov 10
Total with taxes and fees
Oldtown Guesthouse
A single-story house with a covered porch and a chimney, surrounded by trees and a view of a forested hill.

20. Private, clean mountain home near Rocky Gap!

Private, clean mountain home near Rocky Gap!
Cumberland
9.8 out of 10, Exceptional, (18 reviews)
"Clean and comfy cabin. Great wi-fi and everything we needed in the kitchen and bathrooms!"
United States
Alisa S.
$339 nightly
The price is $359
Nov 7 - Nov 8
Total with taxes and fees
Private, clean mountain home near Rocky Gap!
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

8/10 Good
"Make sure you make a reservation to eat in the restaurant even if they tell you you don’t need one"
Angela 2-night trip
Posted 12 hours ago
Rocky Gap Casino & Resort

Find out more about Woodland

Everything you need to know about Woodland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Woodland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Woodland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodland rentals

At Expedia, we put the best Woodland vacation 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 Woodland 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 Woodland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodland. 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 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?

Lakefront, Pet Friendly w Firepit in Quiet Cove: Located near Woodland, this vacation home rental is located on a lake and has a selection of games, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Woodland?

While you're exploring the area, Savage River and Allegheny Passage are a couple of picturesque spots to get outside and enjoy nature. 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.