Oakland Holiday Rentals, Maryland: Private House Rentals

A river flowing through a forest with a waterfall.

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Go beyond your typical stay in Oakland

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Pool

Condo

Hot tub

Family friendly

Cottage

Cabin

Waterpark

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Our top choices for Oakland hotels

1. Baja Motel

Oakland

Richard

฿3,763

฿4,289 total

includes taxes & fees

13 Sept - 14 Sept

2. The Garrett Inn

Oakland

Michael

฿4,148

฿4,779 total

includes taxes & fees

8 Sept - 9 Sept

Romantic Single Room, 1 King Bed, Jetted Tub, Lake View

3. Lake Pointe Inn

McHenry

Steven

฿9,316

฿11,183 total

includes taxes & fees

16 Sept - 17 Sept

Comfort Double Room, 2 Queen Beds, Golf View

4. Alpine Lake Resort

Terra Alta

Frank

฿5,033

฿5,975 total

includes taxes & fees

8 Sept - 9 Sept

Suite, 1 Queen Bed, Accessible, Non Smoking (Mobility, Hearing, Tub w/Grab Bars)

5. Microtel Inn & Suites by Wyndham Hazelton/Bruceton Mills

Bruceton Mills

Stephen m

฿2,519

฿2,821 total

includes taxes & fees

14 Sept - 15 Sept

6. SureStay Plus Hotel by Best Western Keyser

Keyser

John

฿4,330

฿4,850 total

includes taxes & fees

13 Sept - 14 Sept

C 50R - Comfort Cabin, 1 King bed, Pet Friendly, Mountainside (May hear neighbors) | Living area

C 49L - Comfort Cabin, 2 Queen beds, Pet Friendly, Mountainside (May hear neighbors)

C 49R - Comfort Cabin,1 King Bed, Pet Friendly, Mountainside (May hear neighbors) | Living area

7. The Lodges at Sunset Village

McHenry

Virginia

฿7,561

฿8,619 total

includes taxes & fees

9 Sept - 10 Sept

8. Keyser Inn

Keyser

Thomas

฿2,633

฿2,949 total

includes taxes & fees

8 Sept - 9 Sept

Suite- The Historic Building | Living area

9. The Casselman Inn

Grantsville

Chris

฿2,824

฿3,220 total

includes taxes & fees

8 Sept - 9 Sept

10. Comfort Inn Grantsville-Deep Creek Lake

Grantsville

JUDITH

฿3,878

฿4,421 total

includes taxes & fees

9 Sept - 10 Sept

11. LakeFront Lodge

McHenry

Tony

฿6,415

฿7,313 total

includes taxes & fees

6 Oct - 7 Oct

Cottage, Multiple Beds, Kitchen | View from room

12. Abrams Creek Center

Elk Garden

Bill

฿2,169

฿3,200 total

includes taxes & fees

8 Sept - 9 Sept

Deluxe Suite, 2 Bedrooms | Private kitchen

13. The Inn at Canaan

Davis

Marina

฿3,407

฿3,884 total

includes taxes & fees

12 Sept - 13 Sept

14. Cannon Hill Inn

Rowlesburg

Brian

฿2,518

฿3,927 total

includes taxes & fees

15 Sept - 16 Sept

Family Suite, Private Bathroom (Trey Run #5)

15. River House Lodge

Rowlesburg

Lora

฿3,179

฿4,635 total

includes taxes & fees

7 Oct - 8 Oct

16. Mountaineer Motel

Mount Storm

Jorge

฿3,195

฿3,579 total

includes taxes & fees

8 Sept - 9 Sept

17. The Lodge at Wisp Resort

McHenry

Thein

฿8,677

฿10,130 total

includes taxes & fees

8 Sept - 9 Sept

18. Nemacolin

Nemacolin

Marvin

฿25,956

฿30,521 total

includes taxes & fees

14 Sept - 15 Sept

19. Cozy Anchors Away Cabin Hideaway w/ Fire Pit!

Parsons

Jack

฿4,543

฿7,516 total

includes taxes & fees

9 Sept - 10 Sept

20. Modern Homestead Guest House

Reedsville

dulce

฿4,237

฿4,533 total

includes taxes & fees

8 Sept - 9 Sept

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Holiday Rentals in Oakland

Apartment

Deep Creek Lake Townhome w/ Deck & Water Views

Oakland

"very clean and a great view. The location is perfect "

Cabin

Strawberry Fields by Taylor Made Deep Creek

Oakland

Holiday Home

Bee Tree II by Taylor Made Deep Creek

Oakland

"Lake access, beautiful yard with firepit. Kids and adults had a great time."

Cabin

The Perch by Taylor Made Deep Creek

Paradise Point

"Everything was perfect! Spacious enough for 10 people. Beautiful views!"

Holiday Home

Bears Lair by Taylor Made Deep Creek

Oakland

"The property was more than expected and we had a wonderful time. Everything we wanted to do was within driving distance. Wonderful experience!"

Holiday Home

Chateau Relaxo by Taylor Made Deep Creek

Mountainside

Holiday Home

Laurel Brook 39 by Taylor Made Deep Creek

Oakland

"Nice place ."

Holiday Home

Loft of Luxury by Taylor Made Deep Creek

Oakland

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Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

A waterfall cascading over rocks into a clear pool.

Mountainside

Escape to Mountainside, a tranquil retreat nestled among Thayerville's wooded peaks near Deep Creek Lake. This peaceful mountain community offers a natural haven for travellers seeking quiet solitude. The rustic cabins blend seamlessly with the forested landscape. Nature lovers will find adventure just minutes away at Deep Creek Lake State Park. Nearby attractions include the Lodestone Golf Club and Adventure Sports Centre International. Mountain air carries pine scents while private wooded lots provide natural privacy between holiday homes.

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A river winding through a densely forested area with a small town and a lake.

Paradise Point

Paradise Point delivers the quintessential lake holiday experience on the shores of Deep Creek Lake. This waterfront area features private cabins and holiday homes tucked among towering trees. You'll have direct access to crystal-clear waters for swimming, fishing, and boating. The peaceful setting creates a perfect escape from everyday life. Enjoy morning mist rising off the water and evenings around a crackling campfire. While there are no shops or restaurants within Paradise Point itself, nearby Thayerville offers dining options and supplies for your lakeside retreat.

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The View

The View in Thayerville offers the perfect lakeside retreat with direct access to Deep Creek Lake's crystal-clear waters. Private docks and waterfront homes create a peaceful escape for outdoor enthusiasts. Enjoy swimming, fishing, or kayaking right from your holiday rental's backyard. The surrounding Western Maryland landscape provides stunning natural beauty in every season. Nearby Deep Creek Lake State Park offers hiking trails and scenic mountain vistas. Most homes feature expansive windows that frame magnificent lake views and full kitchens for cosy meals after a day on the water.

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Blakeslee

This quiet area in western Maryland offers a peaceful retreat near Deep Creek Lake's natural beauty. Blakeslee welcomes travellers seeking an authentic small-town American experience away from tourist crowds. The residential community provides a perfect base for outdoor adventures in the surrounding Appalachian forests. Holiday rentals and cabins dot this budget-friendly area where travellers can enjoy mountain views and fresh air. Nearby Deep Creek Lake offers boating, swimming and fishing just a short drive away. Golf enthusiasts will appreciate easy access to Thousand Acres Lakeside Golf Course during their stay.

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Silver Ridge

Silver Ridge offers a peaceful lakeside retreat in the Deep Creek Lake area. This residential community features contemporary and traditional holiday homes nestled among mature trees. You'll appreciate the natural setting with forest surroundings and wildlife viewing opportunities. Many properties provide private docks or lake access. The area serves as an ideal base for outdoor activities. Deep Creek Lake State Park and nearby golf courses are just a short drive away. Crystal-clear mountain lake waters invite swimming, boating, and fishing throughout the seasons. Enjoy stargazing and quiet evenings after days filled with outdoor adventure.

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Stay near popular Oakland attractions

A waterfall cascading over a rocky cliff surrounded by lush greenery.

Swallow Falls State Park

9.8/10 (138 reviews)

Maryland's highest free-falling waterfall cascades 53 feet at Swallow Falls State Park. Wander through ancient hemlock forests and listen to the soothing rush of water along well-maintained trails.

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A log cabin with a stone chimney, surrounded by snow-covered ground and trees.

Herrington Manor State Park

9.4/10 (12 reviews)

Nestled in Garrett County, Herrington Manor State Park features a pristine 53-acre lake for swimming, boating, and fishing. Reserve one of the 20 furnished log cabins for a woodland retreat with access to scenic trails.

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Lower Deep Creek Heritage Conservation Fund Site

This 106.5-acre park offers tranquil trails through lush Maryland landscapes for both leisurely strolls and challenging hikes. Explore diverse ecosystems and seasonal beauty with comfortable shoes and water in hand.

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Ruth Enlow Library of Garrett County

The Ruth Enlow Library has served as Oakland's literary hub since 1915, offering resources and community programmes. Browse the diverse collection or join their seasonal reading events in this welcoming space.

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Broadford Park

Nestled around a scenic lake in Oakland, Broadford Park offers family-friendly swimming, boating, and trails. Rent a kayak for a peaceful afternoon or reserve a pavilion for a premium lakeside picnic experience.

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Veteran's Park

Veteran's Park is just one of the places to see in Oakland, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the lakeside.

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Oakland Town Hall

After visiting Oakland Town Hall, make a plan to see the other sights and activities in Oakland. While you're in the area, stroll along the lakeside.

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Glades Park

After visiting Glades Park, make a plan to see the other sights and activities in Oakland. While you're in the area, stroll along the lakeside.

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Learn more about Oakland

Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic city centre where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

See all hotels in Oakland

A waterfall cascading over a rocky cliff into a river surrounded by trees.

Top Oakland Hotel Reviews

The Garrett Inn

10/10 Excellent

"Another good stay at the hotel. Both stays I’ve had here had 0 issues."

Baja Motel

10/10 Excellent

"Clean room and accommodating"

More cheap stays in Oakland

Baja Motel

1501 Maryland Hwy Oakland MD

฿3,763

฿4,289 total

13 Sept - 14 Sept

includes taxes & fees

9/10 Wonderful! (125 reviews)

The Garrett Inn

17848 Garrett Highway Oakland MD

฿4,148

฿4,779 total

8 Sept - 9 Sept

includes taxes & fees

9.8/10 Exceptional! (456 reviews)

Oak Mar Motel

208 N 3rd Street Oakland MD

Get rates

Glencoe by Taylor Made Deep Creek

20526 GARRETT HWY Oakland MD

Get rates

Frequently asked questions

What's the best place to stay in Oakland?

Based on Expedia's traveller preferences, Baja Motel is a top place to stay in Oakland. The Garrett Inn is another good option for your trip. See all available top hotels, or vacation rentals in Oakland.

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes! You'll find that most hotel room reservations are fully refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Oakland.

What is staying in Oakland like?

Visitors to Oakland will definitely enjoy the lakeside setting. Tourists can also enjoy the city's ski areas and ecotours. A top sight in the city is Deep Creek Lake. In Oakland, there are 801 hotels and other accommodation options to choose from. Find out more about Oakland.

What should I do while I'm visiting Oakland?

Natural beauty is on display at Deep Creek Lake, Youghiogheny River and Broadford Park. A couple of additional sights to add to your itinerary are Herrington Manor State Park and Swallow Falls State Park. Take a look at what more there is to see and do in Expedia's Oakland guide.

What's the weather like in Oakland?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Oakland are January, December, February and May, with each month seeing an average of 79 cm of snowfall.

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Book Hotels in Oakland on Expedia.com

Find hotels in Oakland, MD from ฿4,289

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Oakland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Oakland hotels

1. Baja Motel

2. The Garrett Inn

3. Lake Pointe Inn

4. Alpine Lake Resort

5. Microtel Inn & Suites by Wyndham Hazelton/Bruceton Mills

6. SureStay Plus Hotel by Best Western Keyser

7. The Lodges at Sunset Village

8. Keyser Inn

9. The Casselman Inn

10. Comfort Inn Grantsville-Deep Creek Lake

11. LakeFront Lodge

12. Abrams Creek Center

13. The Inn at Canaan

14. Cannon Hill Inn

15. River House Lodge

16. Mountaineer Motel

17. The Lodge at Wisp Resort

18. Nemacolin

19. Cozy Anchors Away Cabin Hideaway w/ Fire Pit!

20. Modern Homestead Guest House

Holiday Rentals in Oakland

Deep Creek Lake Townhome w/ Deck & Water Views

Strawberry Fields by Taylor Made Deep Creek

Bee Tree II by Taylor Made Deep Creek

The Perch by Taylor Made Deep Creek

Bears Lair by Taylor Made Deep Creek

Chateau Relaxo by Taylor Made Deep Creek

Laurel Brook 39 by Taylor Made Deep Creek

Loft of Luxury by Taylor Made Deep Creek

Where to stay in Oakland

Mountainside

Paradise Point

The View

Blakeslee

Silver Ridge

Stay near popular Oakland attractions

Swallow Falls State Park

Herrington Manor State Park

Lower Deep Creek Heritage Conservation Fund Site

Ruth Enlow Library of Garrett County

Broadford Park

Veteran's Park

Oakland Town Hall

Glades Park

Learn more about Oakland

Top Oakland Hotel Reviews

The Garrett Inn

Baja Motel

More cheap stays in Oakland

Baja Motel

The Garrett Inn

Oak Mar Motel

Glencoe by Taylor Made Deep Creek

Frequently asked questions

Explore a world of travel with Expedia

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