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Woodland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Woodland vacation rentals

A two-story building with a green exterior, a black front door, and a small balcony with a metal railing.

1. 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
9.4 out of 10, Exceptional, (33 reviews)
"Lovely place, had all we needed for a comfortable stay. Thanks!"
United States
Molly M.
$200 nightly
The price is $226
Oct 4 - Oct 5
Total with taxes and fees
5 minute walk to downtown. Cozy family sized home with everything you need.
A covered patio with a table and chairs, a hanging basket, and a satellite dish.

2. 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, (63 reviews)
"Host was very polite and helpful!"
United States
Quintin
$165 nightly
The price is $175
Sep 29 - Sep 30
Total with taxes and fees
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
A modern kitchen with a white island, black chairs, and a view of the outdoors.

3. 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
$205 nightly
The price is $217
Sep 29 - Sep 30
Total with taxes and fees
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
A pond with cattails and a white boat.

4. 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.
$125 nightly
The price is $133
Sep 30 - Oct 1
Total with taxes and fees
BIG D's POND & North Branch of the Potomac river Camping.
A cozy room with a wooden floor, a white bed, a sofa, and a small table.

5. Loft two story with first floor workout room, WIFI, complete cottage to yourself

Loft two story with first floor workout room, WIFI, complete cottage to yourself
Grantsville
9.8 out of 10, Exceptional, (43 reviews)
"Everything was lovely! The loft was stocked with everything we needed, it was spotlessly clean, and very comfortable."
United States
Leanna B.
$192 nightly
The price is $203
Sep 29 - Sep 30
Total with taxes and fees
Loft two story with first floor workout room, WIFI, complete cottage to yourself
A bedroom with a large bed, wooden headboard, two bedside tables with lamps, a floral-patterned rug, and a window with curtains.

6. Right off the bike trail.

Right off the bike trail.
Meyersdale
9.6 out of 10, Exceptional, (118 reviews)
"We loved everything about this house: the spaciousness, cleanliness, location, quiet and comfort. It had everything we needed and Karen was a great hostess."
United States
Kathy
$125 nightly
The price is $138
Oct 1 - Oct 2
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.

7. 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, (51 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
$180 nightly
The price is $191
Sep 30 - Oct 1
Total with taxes and fees
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A deck with a white railing, a table, and a view of a forested landscape.

8. 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, (3 reviews)
"This was a really lovely place to stay on a quick trip to Cumberland. It’s in a quiet neighborhood with a great Mountain View off the back deck. The property was clean and the owner was communicative. Convenient to town and the scenic railroad. The only complaint I have was the thermostat was auto set to a temp that was too high for the summer, and I had to wake up twice to make it cooler. Other than that it really is exactly as advertised and I would stay again."
United States
Kasey G.
$180 nightly
The price is $191
Sep 29 - Sep 30
Total with taxes and fees
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

9. 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.
$175 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A living room with a brown leather sofa, a blue couch with patterned pillows, a coffee table, and a wooden floor.

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, (17 reviews)
"Lovely place! "
United States
Courtney N.
$170 nightly
The price is $192
Sep 30 - Oct 1
Total with taxes and fees
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
A wooden interior with a spiral staircase, a kitchen area, and a dining space.

11. 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, (59 reviews)
"Awesome house. And great location "
United States
Richard M.
$229 nightly
The price is $243
Oct 4 - Oct 5
Total with taxes and fees
Private Home in Garrett County, surrounded by trees, fields and farmland.
An outdoor wooden deck with seating, a large tree, and a glass-enclosed room with a bench.

12. Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit

Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
Springfield
10.0 out of 10, Exceptional, (45 reviews)
"Excellent stay at this cabin, extremely clean, smooth check in and out process, and all amenities were available plus a well stocked kitchen. Highly recommended stay for a nice quiet getaway. "
United States
Alex K.
$313 nightly
The price is $314
Sep 29 - Sep 30
Total with taxes and fees
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

13. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
$195 nightly
The price is $207
Sep 29 - Sep 30
Total with taxes and fees
Oldtown Guesthouse
A kitchen with white tiled backsplash, wooden shelves holding glassware, and a coffee maker on the counter.

14. 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, (121 reviews)
"Everything we expected and more. Visited relatively early in the Spring so we're coming back in June to make better use of outdoor dining, etc. The cabin was super cozy and we made full use of the hot tub and fireplace. We really enjoyed our stay."
United States
Steven H.
$270 nightly
The price is $306
Sep 30 - Oct 1
Total with taxes and fees
Secluded, romantic cabin with hot tub on 12 acres of woodland.
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

15. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (9 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
$180 nightly
The price is $191
Oct 19 - Oct 20
Total with taxes and fees
The Suite On Smallwood
A compact kitchen with white cabinetry, a microwave, and a wooden countertop.

16. One of a Kind Custom Airstream / Steps to the GAP bike trail / Meyersdale PA

One of a Kind Custom Airstream / Steps to the GAP bike trail / Meyersdale PA
Meyersdale
10.0 out of 10, Exceptional, (14 reviews)
"Great and fun place to stay in Meyersdale when riding the GAP"
United States
Antoine
$180 nightly
The price is $199
Oct 2 - Oct 3
Total with taxes and fees
One of a Kind Custom Airstream / Steps to the GAP bike trail / Meyersdale PA
A hot tub with a wooden exterior, positioned outdoors with a view of a natural landscape.

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

Tiny House in the Orchard; a Romantic Stay for two
Swanton
$205 nightly
The price is $221
Oct 6 - Oct 7
Total with taxes and fees
Tiny House in the Orchard; a Romantic Stay for two
A bedroom with a bed, desk, chair, and a television.

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

Newly renovated 1905 house, within walking distance to all downtown attractions!
Cumberland
$255 nightly
The price is $271
Oct 13 - Oct 14
Total with taxes and fees
Newly renovated 1905 house, within walking distance to all downtown attractions!
A room with a long wooden desk, four chairs, a woven rug, a ceiling fan, and a mural of flowers on the wall.

19. Knit Inn..

Knit Inn..
Frostburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location! The host was very nice and easy to get a hold of for questions. Would definitely stay here every trip to Frostburg!"
United States
Lori F.
$600 nightly
The price is $636
Oct 2 - Oct 3
Total with taxes and fees
Knit Inn..
A small, single-story, green mobile home with a front porch and a small deck.

20. Trailside Tiny Home Retreat - Steps from GAP Trail

Trailside Tiny Home Retreat - Steps from GAP Trail
Meyersdale
10.0 out of 10, Exceptional, (2 reviews)
"Enjoyed my stay."
United States
Lora V.
$169 nightly
The price is $187
Sep 29 - Sep 30
Total with taxes and fees
Trailside Tiny Home Retreat - Steps from GAP Trail
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

Hampton Inn Cumberland

Hampton Inn Cumberland

10/10 Excellent
"El lugar muy tranquilo todo estuvo bien"
Nancy 2-night trip
Posted less than an hour ago
Hampton Inn Cumberland

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 $133 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: This vacation home near Woodland 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.