Woodland Vacation Rentals

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    Upfront pricing

    We're not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Woodland

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Fridge, microwave, oven, stovetop

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

9.8 out of 10, Exceptional, (17)
"Perfect place to stay...highly recommend. We didn't stay long enough to enjoy the cottage but the time we were there was great."
$168 nightly
The price is $178
Sep 4 - Sep 5
Total with taxes and fees
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Vintage 1960s Cardinal Cottage, w/ hot tub, fire pit, and 5 mins from the Lake
Property grounds

Vintage 1960s Cardinal Cottage, w/ hot tub, fire pit, and 5 mins from the Lake

9.8 out of 10, Exceptional, (32)
"It was an absolute pleasure to stay in this home away from home. The hot tub made for a relaxed time after our daily adventures. "
Vintage 1960s Cardinal Cottage, w/ hot tub, fire pit, and 5 mins from the Lake
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
Outdoor dining

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

2.0 star property
10.0 out of 10, Exceptional, (29)
"We loved staying at this cabin in April. This cabin has so many thoughtful details and beautiful views. Both of my teenagers already want to know when we can come back, which is a glowing recommendation from them as well. Thanks for the great trip!"
$313 nightly
The price is $315
Sep 2 - Sep 3
Total with taxes and fees
Milam Ridge: Modern Cabin Escape. Hot Tub, Covered Deck, Fire Pit
Right off the bike trail.
Fridge, microwave, oven, stovetop

Right off the bike trail.

9.6 out of 10, Exceptional, (89)
"Beds were very comfortable. It was great for our family of six."
$125 nightly
The price is $138
Sep 1 - Sep 2
Total with taxes and fees
Right off the bike trail.
New! Discover Serendipity: Lake Front, Dogs Ok, Pool, Hot Tub!
Property grounds

New! Discover Serendipity: Lake Front, Dogs Ok, Pool, Hot Tub!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great stay!"
New! Discover Serendipity: Lake Front, Dogs Ok, Pool, Hot Tub!
Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen
Interior

Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen

9.8 out of 10, Exceptional, (18)
"It was a fantastic place to stay with a group or a large family."
Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen
Cannon Cliffside River Retreat- FREE WIFI
Fridge, microwave, oven, stovetop

Cannon Cliffside River Retreat- FREE WIFI

10.0 out of 10, Exceptional, (31)
"Property was clean and quiet, matched the description. We enjoyed our trip!"
Cannon Cliffside River Retreat- FREE WIFI
BIG D's POND & North Branch of the Potomac river Camping.
Pool

BIG D's POND & North Branch of the Potomac river Camping.

10.0 out of 10, Exceptional, (3)
"Big D'S Pond is beautiful and the owner, is very kind and helpful. We had an amazing time!"
$107 nightly
The price is $114
Sep 1 - Sep 2
Total with taxes and fees
BIG D's POND & North Branch of the Potomac river Camping.
Private Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit
Game room

Private Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit

9.0 out of 10, Wonderful, (96)
"Despite the weather, we had a wonderful stay. The house was very clean. The views were amazing and makes you feel secluded. It was the perfect location. The only thing I could say is we wish the indoor pool was a little warmer but we still made the best of it. Would absolutely stay again!! "
Private Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit
Awesome New Property/ CANAL RIVER RETREAT
Lake

Awesome New Property/ CANAL RIVER RETREAT

9.8 out of 10, Exceptional, (112)
"Easy access to trails. Quiet spot just ouside Cumberland. "
Awesome New Property/ CANAL RIVER RETREAT
The Lodge, a Cozy Lodge Cabin by the GAP Trail & view of the Sand Patch grade.
Terrace/patio

The Lodge, a Cozy Lodge Cabin by the GAP Trail & view of the Sand Patch grade.

10.0 out of 10, Exceptional, (1)
"A beautiful, tucked away cabin that gives you a relaxing getaway. We had a little trouble finding it (if you go on the dirt road, you've gone too far) but owners say they are putting up more signs. It was definitely worth the small trek in as there was a large hot tub, plenty of beds to choose from, and a cozy atmosphere. They had a small refrigerator, kitchenette space/supplies, and microwave/coffee maker. We would definitely recommend staying here! Oh, there is a train track nearby so you will...
$257 nightly
The price is $284
Sep 1 - Sep 2
Total with taxes and fees
The Lodge, a Cozy Lodge Cabin by the GAP Trail & view of the Sand Patch grade.
Cozy Cabin with Hot Tub, Lake Access, Screened Porch, & Firepit
Terrace/patio

Cozy Cabin with Hot Tub, Lake Access, Screened Porch, & Firepit

9.0 out of 10, Wonderful, (46)
"Property was very nice, very spacious with plenty of room."
Cozy Cabin with Hot Tub, Lake Access, Screened Porch, & Firepit
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
Fridge, microwave, oven, stovetop

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

10.0 out of 10, Exceptional, (294)
"Perfect set up for our families and children to stay for a nearby wedding. Quick drive to Deep Creek Lake, and multiple separate bedrooms with individual heating/cooling options. Plenty of fun extras for the kids and two living rooms to have adult space and kid space. Kitchen table was great! Rainy trip so not a lot of opportunity for outdoor fun but everything looked great!"
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
Top of the GAP guesthouse on the Eastern Continental Divide.
Fridge, oven, stovetop, dishwasher

Top of the GAP guesthouse on the Eastern Continental Divide.

$199 nightly
The price is $220
Sep 2 - Sep 3
Total with taxes and fees
Top of the GAP guesthouse on the Eastern Continental Divide.
Spacious Victorian Home 2nd floor apartment
Exterior

Spacious Victorian Home 2nd floor apartment

10.0 out of 10, Exceptional, (49)
"Enjoyed our stay for a weekend trip"
$111 nightly
The price is $122
Sep 1 - Sep 2
Total with taxes and fees
Spacious Victorian Home 2nd floor apartment
Oldtown Guesthouse
Fridge, microwave, oven, stovetop

Oldtown Guesthouse

10.0 out of 10, Exceptional, (23)
"Very clean and charming."
$170 nightly
The price is $180
Sep 10 - Sep 11
Total with taxes and fees
Oldtown Guesthouse
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Smart TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (99)
"Property was just as described, we had a great time, spent time riding bikes on the C&O Canal NHP, and hiking at Rocky Gap State Park."
$284 nightly
The price is $321
Sep 1 - Sep 2
Total with taxes and fees
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Full home near C&O! Perfect for bikers or families!
Fridge, microwave, oven, stovetop

Full home near C&O! Perfect for bikers or families!

9.6 out of 10, Exceptional, (15)
"Super clean. Love the neighborhood and older houses. "
$222 nightly
The price is $235
Sep 3 - Sep 4
Total with taxes and fees
Full home near C&O! Perfect for bikers or families!
Waterfront Retreat: Lakefront, Golf Area, Indoor Pool, Dock Slip!
Interior

Waterfront Retreat: Lakefront, Golf Area, Indoor Pool, Dock Slip!

10.0 out of 10, Exceptional, (8)
"Great property - recommend."
Waterfront Retreat: Lakefront, Golf Area, Indoor Pool, Dock Slip!
Hilltop 10 acre Cabin Retreat Getaway - WiFi!
Property grounds

Hilltop 10 acre Cabin Retreat Getaway - WiFi!

9.2 out of 10, Wonderful, (35)
"Rented house for a work trip and it was great"
Hilltop 10 acre Cabin Retreat Getaway - WiFi!
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

Find out more about Woodland

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 $114 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym): This vacation home near Woodland is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.