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Woodland Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Woodland holiday rentals

A bedroom with a large bed, wooden headboard, two bedside tables with lamps, a floral-patterned rug, and a window with curtains.

1. Right off the bike trail.

Right off the bike trail.
Meyersdale
9.6 out of 10, Exceptional, (121 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
The price is AU$200
includes taxes & fees
16 Oct - 17 Oct
Right off the bike trail.
A two-story building with a green exterior, a black front door, and a small balcony with a metal railing.

2. 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, (34 reviews)
"Lovely place, had all we needed for a comfortable stay. Thanks!"
United States
Molly M.
The price is AU$342
includes taxes & fees
13 Oct - 14 Oct
5 minute walk to downtown. Cozy family sized home with everything you need.
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, (53 reviews)
"Great stay"
United States
Michael R.
The price is AU$279
includes taxes & fees
15 Oct - 16 Oct
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, (64 reviews)
"Host was very polite and helpful!"
United States
Quintin
The price is AU$253
includes taxes & fees
18 Oct - 19 Oct
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
A residential area with a two-story house featuring a porch and a red car parked in front.

5. The Grateful Trail House- Weir

The Grateful Trail House- Weir
Cumberland
The Grateful Trail House- Weir
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

6. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (10 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is AU$298
includes taxes & fees
22 Oct - 23 Oct
The Suite On Smallwood
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

7. 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.
The price is AU$289
includes taxes & fees
25 Oct - 26 Oct
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.

8. 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, (18 reviews)
"Lovely place! "
United States
Courtney N.
The price is AU$280
includes taxes & fees
25 Oct - 26 Oct
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.

9. 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)
"Awesome house. And great location "
United States
Richard M.
The price is AU$356
includes taxes & fees
15 Oct - 16 Oct
Private Home in Garrett County, surrounded by trees, fields and farmland.
A cozy room with a wooden floor, a white bed, a sofa, and a small table.

10. The Loft Private Guesthouse, Gym & Workspace

The Loft Private Guesthouse, Gym & Workspace
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.
The price is AU$378
includes taxes & fees
13 Oct - 14 Oct
The Loft Private Guesthouse, Gym & Workspace
A pond with cattails and a white boat.

11. 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.
The price is AU$193
includes taxes & fees
13 Oct - 14 Oct
BIG D's POND & North Branch of the Potomac river Camping.
A bedroom with a bed, desk, chair, and a television.

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

Newly renovated 1905 house, within walking distance to all downtown attractions!
Cumberland
The price is AU$385
includes taxes & fees
27 Oct - 28 Oct
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.

13. 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
8.6 out of 10, Excellent, (7 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.
The price is AU$311
includes taxes & fees
15 Oct - 16 Oct
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A modern kitchen with a white island, black chairs, and a view of the outdoors.

14. 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
The price is AU$351
includes taxes & fees
13 Oct - 14 Oct
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
A hot tub with a wooden exterior, positioned outdoors with a view of a natural landscape.

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

Tiny House in the Orchard; a Romantic Stay for two
Swanton
The price is AU$319
includes taxes & fees
20 Oct - 21 Oct
Tiny House in the Orchard; a Romantic Stay for two
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, (124 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.
The price is AU$471
includes taxes & fees
3 Nov - 4 Nov
Secluded, romantic cabin with hot tub on 12 acres of woodland.
A room with a long wooden desk, four chairs, a woven rug, a ceiling fan, and a mural of flowers on the wall.

17. 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.
The price is AU$935
includes taxes & fees
22 Oct - 23 Oct
Knit Inn..
An outdoor wooden deck with seating, a large tree, and a glass-enclosed room with a bench.

18. 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)
"Lovely place everyone enjoyed staying here, very clean and excellent location"
United States
William R.
The price is AU$471
includes taxes & fees
20 Oct - 21 Oct
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.

19. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (36 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
The price is AU$312
includes taxes & fees
2 Nov - 3 Nov
Oldtown Guesthouse
An outdoor hot tub with a fire, a wicker basket with bread, and a bottle of wine.

20. Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres

Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
Keyser
10.0 out of 10, Exceptional, (1 review)
"My wife and I had a great stay at this property, we would happily visit again!"
United States
Cole D.
The price is AU$569
includes taxes & fees
13 Oct - 14 Oct
Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
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

LaVale Inn Cumberland Area

LaVale Inn Cumberland Area

10/10 Excellent
"I enjoyed my stay, friendly staff, would stay here again."
David 1-night trip
Posted 2 hours ago
LaVale Inn Cumberland Area

Find out more about Woodland

Everything you need to know about Woodland holiday rentals

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

Woodland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodland holiday rentals we have selected for you start as low as AU$193 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodland rentals

At Expedia, we put the best Woodland holiday 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 holiday.

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 holiday rental in Woodland?

Yes, there are holiday rentals close to the most popular sights in Woodland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Woodland has to offer?

Lakefront, Pet Friendly w Firepit in Quiet Cove: This holiday home rental outside of Woodland is located on a lake, and has a selection of games, a BBQ 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 wider area, you’ll find Noah's Ark and Frostburg State University.

What are holiday rentals like in Woodland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodland. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family gatherings.