Woodland Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Woodland holiday rentals

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, (39 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 NZ$565
includes taxes & fees
11 June - 12 June
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)
"This was a wonderful place clean, private, spacious and convenient will definitely recomend"
United States
Karen C.
The price is NZ$313
includes taxes & fees
10 June - 11 June
Oldtown Guesthouse
Shower, hair dryer, towels, soap

Right off the bike trail.

Right off the bike trail.
Meyersdale
9.6 out of 10, Exceptional, (107 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 NZ$237
includes taxes & fees
13 June - 14 June
Right off the bike trail.
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, (39 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 NZ$353
includes taxes & fees
14 June - 15 June
Loft two story with first floor workout room, WIFI, complete cottage to yourself
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, (4 reviews)
"Great place to stay!! Very clean and extremely close to local attractions. "
United States
Mitchum
The price is NZ$374
includes taxes & fees
9 July - 10 July
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
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, (57 reviews)
"Place was clean and comfortable."
United States
Marc R.
The price is NZ$301
includes taxes & fees
13 June - 14 June
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
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, (115 reviews)
"We had an excellent stay! The home was clean, comfortable and exactly as described. We would stay here again and recommend it. "
United States
Lisa S.
The price is NZ$548
includes taxes & fees
16 June - 17 June
Secluded, romantic cabin with hot tub on 12 acres of woodland.
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, (36 reviews)
"House was clean and neat. Quite neighborhood "
United States
Roxana F.
The price is NZ$328
includes taxes & fees
23 June - 24 June
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
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, (12 reviews)
"Great and fun place to stay in Meyersdale when riding the GAP"
United States
Antoine
The price is NZ$322
includes taxes & fees
10 June - 11 June
One of a Kind Custom Airstream / Steps to the GAP bike trail / Meyersdale PA
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, (47 reviews)
"Such a great place!! Very peaceful, nice amenities, stocked kitchen. Much bigger than expected. I would definitely stay there again and tell others who are headed that way!!"
United States
Aidan43 C.
The price is NZ$460
includes taxes & fees
10 June - 11 June
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
The price is NZ$301
includes taxes & fees
10 June - 11 June
Trailside Tiny Home Retreat - Steps from GAP Trail
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 NZ$390
includes taxes & fees
23 June - 24 June
5 minute walk to downtown. Cozy family sized home with everything you need.
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 NZ$195
includes taxes & fees
11 June - 12 June
BIG D's POND & North Branch of the Potomac river Camping.
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 NZ$300
includes taxes & fees
14 June - 15 June
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
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
The price is NZ$623
includes taxes & fees
8 July - 9 July
Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres
Exterior

Luxury Chalet: Hot Tub + Sauna + Tesla EV + Starlink. Mins to Wisp!

Luxury Chalet: Hot Tub + Sauna + Tesla EV + Starlink. Mins to Wisp!
Swanton
10.0 out of 10, Exceptional, (6 reviews)
"Everything was beyond expectations. The amenities were fantastic and the views of the mountains were also great. 10/10"
United States
Dave H.
Luxury Chalet: Hot Tub + Sauna + Tesla EV + Starlink. Mins to Wisp!
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, (16 reviews)
"Lovely place! "
United States
Courtney N.
The price is NZ$297
includes taxes & fees
14 June - 15 June
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Shower, hair dryer, towels, soap

The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.0 out of 10, Wonderful, (2 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is NZ$267
includes taxes & fees
22 June - 23 June
The Suite On Smallwood
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, (218 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.
Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
Property grounds

Prvt Rm 4, Upper floor, pond view, gas fireplace

Prvt Rm 4, Upper floor, pond view, gas fireplace
Swanton
Prvt Rm 4, Upper floor, pond view, gas fireplace
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

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

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

10/10 Excellent
"The place was very clean and neat. Lots of privacy and we liked that they were kitchen supplies we could use and replace if needed. Lots of ways to relax in seclusion. Also we thought it was super cool that there was a loft with an extra bed, couch, and lots of board games!"
Melzy W. 3-night trip
Posted 7 hours ago
Secluded, romantic cabin with hot tub on 12 acres of woodland.

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 favorite 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 depends 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 NZ$195 per night. Entering your travel dates in the search wizard you might find 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?

Right off the bike trail.: This holiday home rental outside of Woodland is located in a rural location, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.