Latest Vacation Rentals in Oakland MD (587)

Photo for

5 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Majestically situated right along the lakefront, this premier property will provide you with long lasting vacation memories. Enjoy star gazing and amazing views from the many decks or leave your...

Created Nov 27, 2022

Photo for

5 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Please note: This community complies with Garret County's Noise Ordinance and enforces quiet hours from 10:00PM to 8:00AM. We ask for your consideration, as this community contains full time...

Created Nov 27, 2022

Photo for

2 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Name: Tolson Cabin | Bedrooms: 2 | Bathrooms: 1 | Sleeps: 6 | Access: Lake Front | Dogs Welcome Max. 2 | MUST BE 24+ YEARS TO RENT | Free WIFI Provided*Bed linens & bath towels provided w/rental....

Created Nov 27, 2022

Photo for

2 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Loft of Luxury is a spectacular 2 level townhome located within walking distance to some of Deep Creek's favorite shops! This home is the perfect choice for the small family retreat or a couple's...

Created Nov 27, 2022

Photo for

6 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Name: Always in Season | Bedrooms: 6 | Bathrooms: 5 | Sleeps: 14 | Access: Lake Front | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI Provided*Bed linens & bath towels provided...

Created Nov 27, 2022

Photo for

4 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Brimming with lots of recent updates, On the Rocks is ready to host your next Deep Creek Lake vacation! It is in the picturesque Gallatin Woods community that is just minutes from area activities....

Created Nov 27, 2022

Photo for

4 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Come on in to Blue Bear Lake House! This newly renovated home is full of delights, both big and small. Some of our standout features include the two fireplaces, lower level wet bar, upper level...

Created Nov 27, 2022

Photo for

4 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Memory Lane is a home designed to bring friends and family together for fun and laughter. Recently updated, it includes new appliances and Rokus for all TVs. Tucked among gracious, blossomed trees...

Created Nov 27, 2022

Photo for

4 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Name: Crowd Pleaser | Bedrooms: 4 | Bathrooms: 4.5 | Sleeps: 11 | Access: Lake Access | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI Provided*Bed linens & bath towels provided...

Created Nov 27, 2022

Photo for

4 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Name: Paradise Cove Vista | Bedrooms: 4 | Bathrooms: 3.5 | Sleeps: 10 | Access: Lake Access | Pets Not Permitted | MUST BE 30+ YEARS TO RENT | Free WIFI Provided*Bed linens & bath towels provided...

Created Nov 27, 2022

Photo for

8 Br Private Vacation Home Vacation Rental In Mchenry, Maryland

WINTER/SPRING/SUMMER/FALL -we are 4 Season!!!! Highland Manor is next door to WISP and in the Spring and Summer - we now have a DOCK SLIP as well! Summer Weekly rentals include family passes to the...

Created Nov 27, 2022

Photo for

1 Br Condo Vacation Rental In Oakland, Maryland

These two level units come with a full kitchen, living and dining area also comes with a great fireplace and scenic balcony all on the main level. The upper level has a bath and a bedroom with 1...

Created Nov 27, 2022

Photo for

6 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Under new ownership as of May 2022, this roomy chalet has been refreshed with new paint, carpet, bedding, furniture, smart TVs, and kitchen items as well as sound machine/night light/ Bluetooth...

Created Nov 27, 2022

Photo for

1 Br Apart-Hotel Vacation Rental In Oakland, Maryland

This luxury Studio Standard View suite accommodates four and offers the comforts of home at an affordable price. This suite is perfect for a romantic getaway offering a cozy gas fireplace. For...

Created Nov 27, 2022

Photo for

3 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Surround yourself with natural beauty at this wonderful home located in the cozy, lakefront Timberloft community at the heart of Deep Creek Lake. Two of the three bedrooms are suites making it a...

Created Nov 27, 2022

Photo for

3 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Nestled in a quiet and wooded original lake neighborhood on the west wide of Deep Creek Lake, our home Lake View Escape is a perfect spot for your relaxing year round retreat. Our spacious property...

Created Nov 27, 2022

Photo for

3 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Unwind from the buzz of the city and retreat into Marylands northwest corner for a rejuvenating stay at this Oakland home! There are plenty of outdoor adventure spots nearby such as Deep Creek Lake...

Created Nov 27, 2022

Photo for

3 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Tucked among towering trees, Knotty Pines offers you a classic mountain getaway with lots of opportunities to make lasting memories with your favorite people. Tastefully decorated, the great room...

Created Nov 27, 2022

Photo for

5 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Name: Knee Deep Retreat | Bedrooms: 5 | Bathrooms: 3 | Sleeps: 14 | Access: Lake Access | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI Provided*Bed linens & bath towels provided...

Created Nov 27, 2022

Photo for

4 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Experience the beauty of Deep Creek Lake at Fox Den, a charming A-frame cottage that offers a treasured chance to unwind. Both romance-seekers and those in pursuit of inner peace will relish time...

Created Nov 27, 2022

Photo for

3 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Notice: We now limit reservations to 12 months in advance. If you would like to book for the same time next year, make your request during your stay, otherwise it will be available to the public...

Created Nov 27, 2022

Photo for

1 Br Condo Vacation Rental In Oakland, Maryland

Top Condo view with a panoramic view of Deep Creek Lake, a breath-taking view of the beautiful countryside. This unit has a kitchen, living and dining area, bath, and balcony on the main level....

Created Nov 27, 2022

Photo for

5 Br Private Vacation Home Vacation Rental In Oakland, Maryland

Situated in the heart of Deep Creek Lake, Canoe Cottage offers you amazing lake views, spectacular sunrises and easy access to favorite activities! Upon entering the spacious main level, your eyes...

Created Nov 27, 2022

Photo for

5 Br Private Vacation Home Vacation Rental In Oakland, Maryland

The Birch Bower is a stunning, one-of-a-kind property on Deep Creek Lake. Situated on one of the lakes quietest, most private points, this design-forward, newly-built home features more than 600 of...

Created Nov 27, 2022

Photo for

2 Br Cabin Vacation Rental In Oakland, Maryland

Name: No Worries | Bedrooms: 2 | Bathrooms: 1 | Sleeps: 6 | Access: Lake Area | Dogs Welcome Max. 2 | MUST BE 24+ YEARS TO RENT | Free WIFI Provided*Bed linens & bath towels provided w/rental. No...

Created Nov 27, 2022

Page 1 out of 24
Page 1 out of 24
1 2 3 4 5
goodideazs, LLC is not affiliated with the authors of this post nor is it responsible for its content, the accuracy and authenticity of which should be independently verified.