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Woodland Holiday Rentals

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Check prices for these dates

In two weeks
24 July - 26 July
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Woodland holiday rentals

4 bedrooms, WiFi, bed sheets

Right off the bike trail.

Right off the bike trail.
Meyersdale
9.6 out of 10, Exceptional, (110 reviews)
"Old place, felt like staying at my grandparents, but clean and everything worked. The hose was turned off but Karen came out and turned it on quickly and was very nice. We very much enjoyed our stay and would stay there again if in town."
United States
Samuel
The price is AU$201
includes taxes & fees
13 July - 14 July
Right off the bike trail.
Terrace/patio

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, (58 reviews)
"Place was clean and comfortable."
United States
Marc R.
The price is AU$254
includes taxes & fees
17 July - 18 July
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
Outdoor dining

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, (38 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.
The price is AU$475
includes taxes & fees
16 July - 17 July
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
Fridge, microwave, oven, stovetop

Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (33 reviews)
"Everything was amazing. Fresh cookies and flowers decorated the house. Beautiful location. Nice spot to pack and turn around a big truck."
United States
Joshua E.
The price is AU$292
includes taxes & fees
14 July - 15 July
Oldtown Guesthouse
Interior

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, (116 reviews)
"We had a very relaxing stay! Loved the hot tub and the fireplace!"
United States
Jeanelle B.
The price is AU$455
includes taxes & fees
20 July - 21 July
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Interior

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, (40 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$300
includes taxes & fees
13 July - 14 July
Loft two story with first floor workout room, WIFI, complete cottage to yourself
Fridge, microwave, coffee/tea maker, toaster

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, (13 reviews)
"Great and fun place to stay in Meyersdale when riding the GAP"
United States
Antoine
The price is AU$249
includes taxes & fees
25 July - 26 July
One of a Kind Custom Airstream / Steps to the GAP bike trail / Meyersdale PA
Interior

The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.6 out of 10, Exceptional, (4 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is AU$247
includes taxes & fees
14 July - 15 July
The Suite On Smallwood
Pool

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, (3 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$166
includes taxes & fees
21 July - 22 July
BIG D's POND & North Branch of the Potomac river Camping.
Property grounds

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, (39 reviews)
"House was very clean and comfortable, and very convenient to downtown Cumberland. "
United States
Larry M.
The price is AU$277
includes taxes & fees
16 July - 17 July
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Dining

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, (5 reviews)
"Great place to stay!! Very clean and extremely close to local attractions. "
United States
Mitchum
The price is AU$324
includes taxes & fees
13 July - 14 July
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
Fridge, microwave, oven, stovetop

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, (8 reviews)
"Easy walk into town and the train station."
United States
Kathy M.
The price is AU$296
includes taxes & fees
14 July - 15 July
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
Interior

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, (51 reviews)
"Awesome house. And great location "
United States
Richard M.
The price is AU$386
includes taxes & fees
19 July - 20 July
Private Home in Garrett County, surrounded by trees, fields and farmland.
Exterior

Trailside Tiny Home Retreat - Steps from GAP Trail

Trailside Tiny Home Retreat - Steps from GAP Trail
Meyersdale
10.0 out of 10, Exceptional, (1 review)
"Great proximity to the GAP trail and easy walk into town for meals."
United States
Mike J.
The price is AU$244
includes taxes & fees
13 July - 14 July
Trailside Tiny Home Retreat - Steps from GAP Trail
TV

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.
The price is AU$283
includes taxes & fees
14 July - 15 July
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Exterior detail

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, (31 reviews)
"Great location. Lots of space. Easy parking."
United States
Mary
The price is AU$335
includes taxes & fees
13 July - 14 July
5 minute walk to downtown. Cozy family sized home with everything you need.
Games room

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

Run away to the mountains of WV! Peaceful country home is waiting for you!
Springfield
9.8 out of 10, Exceptional, (56 reviews)
"Fantastic WV getaway! Place was lovely - well accommodated kitchen and lovely private property. Would come back!"
United States
Mike S.
The price is AU$492
includes taxes & fees
31 July - 1 Aug
Run away to the mountains of WV! Peaceful country home is waiting for you!
Outdoor spa tub

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$517
includes taxes & fees
14 July - 15 July
Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
View from property

Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake

Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
Accident
10.0 out of 10, Exceptional, (219 reviews)
"The hosts are amazing. This is great spot, we shall be back in summer. The best hosts we have had in deep creek lake area. "
United States
Sid D.
The price is AU$955
includes taxes & fees
14 July - 15 July
Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
Fridge, microwave, oven, stovetop

Rustic Oasis for the Family - 6 min walk to Downtown

Rustic Oasis for the Family - 6 min walk to Downtown
Cumberland
10.0 out of 10, Exceptional, (2 reviews)
"Property and location just as advertised. Owner was very good about communicating and letting you know he was available if any issues came up (which they did not). Would stay there again!"
United States
Bruce H.
The price is AU$542
includes taxes & fees
15 July - 16 July
Rustic Oasis for the Family - 6 min walk to Downtown
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

Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

8/10 Good
"………………………..pppp.gggggggggsssssssssss"
Joseph 1-night trip
Posted 2 hours ago
Ramada by Wyndham Cumberland Downtown

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$166 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?

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi: This holiday home rental outside of Woodland is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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 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.