Search Holiday Rentals in Woodland

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Woodland holiday 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
The price is £226
includes taxes & fees
1 Dec - 2 Dec
Mid Century-Modern Retreat Great Allegheny Passage
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
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay when visiting Frostburg"
United States
Sofia
The price is £168
includes taxes & fees
13 Nov - 14 Nov
5 minute walk to downtown. Cozy family sized home with everything you need.
A bedroom with a large bed, wooden headboard, two bedside tables with lamps, a floral-patterned rug, and a window with curtains.

3. 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
The price is £98
includes taxes & fees
12 Nov - 13 Nov
Right off the bike trail.
A modern interior with a dining area, kitchen, and a red-framed sliding door.

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

Mountain-View Condo w/ Patio & Free Parking
Cumberland
The price is £167
includes taxes & fees
18 Nov - 19 Nov
Mountain-View Condo w/ Patio & Free Parking
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.
The price is £145
includes taxes & fees
18 Nov - 19 Nov
The Suite On Smallwood
A covered patio with a table and chairs, a hanging basket, and a satellite dish.

6. 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, (67 reviews)
"Host was very polite and helpful!"
United States
Quintin
The price is £126
includes taxes & fees
12 Nov - 13 Nov
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
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, (57 reviews)
"comfortable cottage. In between most activity areas."
United States
WILSON
The price is £139
includes taxes & fees
12 Nov - 13 Nov
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A wooden deck with a hot tub, a table, and benches.

8. 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
The price is £161
includes taxes & fees
18 Nov - 19 Nov
Peaceful and relaxing three bedroom home with hot tub, right beside I-68
A kitchen with a central island, bar stools, a refrigerator, and a window with blinds.

9. 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.
The price is £190
includes taxes & fees
2 Dec - 3 Dec
Newly renovated 1905 house, within walking distance to all downtown attractions!
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

10. 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 £144
includes taxes & fees
13 Nov - 14 Nov
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
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
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!! Very clean and extremely close to local attractions. "
United States
Mitchum
The price is £177
includes taxes & fees
12 Nov - 13 Nov
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
A house with a covered porch, a large tree in front, and a picnic table.

12. 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 £94
includes taxes & fees
14 Nov - 15 Nov
BIG D's POND & North Branch of the Potomac river Camping.
A blue door with the number 137, a wreath, and a mailbox.

13. 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.
The price is £142
includes taxes & fees
20 Nov - 21 Nov
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
A deck with a white railing, a table, and a view of a forested landscape.

14. 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
9.0 out of 10, Wonderful, (11 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 £154
includes taxes & fees
17 Nov - 18 Nov
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A wooden interior with a spiral staircase, a kitchen area, and a dining space.

15. 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, (63 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.
The price is £172
includes taxes & fees
12 Nov - 13 Nov
Private Home in Garrett County, surrounded by trees, fields and farmland.
A modern interior with a sofa, ottoman, and kitchen area, large windows with a forest view, and pendant lighting.

16. Riverside Honeymoon Escape. Riverfront Hot Tub!

Riverside Honeymoon Escape. Riverfront Hot Tub!
Grantsville
The price is £273
includes taxes & fees
12 Nov - 13 Nov
Riverside Honeymoon Escape. Riverfront Hot Tub!
A cabin with a deck, a hot tub, and a view of the surrounding forest.

17. Romantic Riverside Getaway! Riverview Hot Tub!

Romantic Riverside Getaway! Riverview Hot Tub!
Grantsville
The price is £285
includes taxes & fees
16 Nov - 17 Nov
Romantic Riverside Getaway! Riverview Hot Tub!
A modern kitchen with a dining area, large windows, and a stone fireplace.

18. 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.
The price is £230
includes taxes & fees
18 Nov - 19 Nov
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.

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

Tiny House in the Orchard; a Romantic Stay for two
Swanton
The price is £164
includes taxes & fees
16 Nov - 17 Nov
Tiny House in the Orchard; a Romantic Stay for two
A corridor with a mural, a chandelier, and a brick wall.

20. 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 £472
includes taxes & fees
22 Nov - 23 Nov
Knit Inn..
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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Find holiday rentals that suit your style

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Top Woodland Hotel Reviews

A modern building with a stone facade, large glass entrance, and a covered outdoor area.
Hampton Inn Frostburg

Hampton Inn Frostburg

Hampton Inn Frostburg
Frostburg

10/10 Excellent

Staff were great, room was ideal, maybe a slightly better view rather than wall. Pool and gym were well maintained and breakfast was good range.
United Kingdom
Sinan
Reviewed April 3, 2026
Hampton Inn Frostburg

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, apart-hotels, 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 £50 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?

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.