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Holiday homes in Oakland

Enjoy your stay and find the best Holiday homes in Oakland at affordable prices

Searching for a holiday home in Oakland (Maryland)? Explore a great selection of vacation homes in Oakland to find the one that best fits to your needs, starting from $120.86 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Oakland and region (30 miles)
Secluded Oakland House with Hot Tub and On-Site Hiking in Oakland, USA

Secluded Oakland House with Hot Tub and...

Holiday home in Oakland, Maryland
Featuring a hot tub, Secluded Oakland House with On-Site Hiking! is located in Oakland.
  • Parking
  • Pets allowed

no reviews

from $311.00 Show details »

Private Family Home with Deck, Porch and Forest Views! in Oakland, USA

Private Family Home with Deck, Porch and...

Holiday home in Oakland, Maryland
Boasting a spa bath, Private Family Home with Deck, Porch and Forest Views! is situated in Oakland.
  • Parking
  • Internet facilities
  • Shower
  • Bath
  • TV

Superb 11 Reviews 9.3

from $282.33 Show details »

Oakland Retreat about 13 Mi to Deep Creek Lake! in Oakland, USA

Oakland Retreat about 13 Mi to Deep Cree...

Holiday home in Oakland, Maryland
Featuring a spa bath, Oakland Retreat about 13 Mi to Deep Creek Lake! is located in Oakland.
  • Parking
  • Pets allowed

Superb 4 Reviews 9.3

from $269.67 Show details »

Serenity Chalet in Oakland, USA

Serenity Chalet

Holiday home in Oakland, Maryland
Set in Oakland, Serenity Chalet offers accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $303.14 Show details »

Swallow Falls Cabin #4 in Oakland, USA

Swallow Falls Cabin #4

Holiday home in Oakland, Maryland
Swallow Falls Cabin #4 is located in Oakland.
  • Parking
  • TV
  • Air conditioning
  • Refrigerator
  • Free toiletries

Very good 6 Reviews 8.2

from $341.47 Show details »

Nature's Escape in Oakland, USA

Nature's Escape

Holiday home in Oakland, Maryland
Natures Escape is located in Oakland.
  • Parking
  • Tea/Coffee maker
  • TV
  • Air conditioning
  • Refrigerator

Fabulous 3 Reviews 8.7

from $210.91 Show details »

Swallow Falls Cabin #2 in Oakland, USA

Swallow Falls Cabin #2

Holiday home in Oakland, Maryland
Set in Oakland in the Maryland region, Swallow Falls Cabin #2 has a patio.
  • Parking
  • Tea/Coffee maker
  • TV
  • Air conditioning
  • Refrigerator

Good 13 Reviews 7.4

from $198.46 Show details »

Swallow Falls Cabin #3 in Oakland, USA

Swallow Falls Cabin #3

Holiday home in Oakland, Maryland
Boasting air-conditioned accommodation with a patio, Swallow Falls Cabin #3 is set in Oakland.
  • Parking
  • Tea/Coffee maker
  • TV
  • Air conditioning
  • Refrigerator

Very good 8 Reviews 8.5

from $224.97 Show details »

Bear Paws in Oakland, USA

Bear Paws

Holiday home in Oakland, Maryland
Bear Paws is situated in Oakland.
  • Parking
  • Pets allowed
  • Fitness centre

no reviews

from $428.67 Show details »

Paradise at Penn Cove in Oakland, USA

Paradise at Penn Cove

Holiday home in Oakland, Maryland
Located in Oakland, Paradise at Penn Cove provides accommodation with a patio and free WiFi.
  • Parking

no reviews

from $493.00 Show details »

Private Lake Cabin w Deck&Grill, Fire Pit, WiFi! in Terra Alta, USA

Private Lake Cabin w Deck&Grill, Fire Pi...

Holiday home in Terra Alta near Oakland, Maryland , Teaberry Lane 83
Located in Terra Alta in the West Virginia region, Private Lake Cabin w Deck&Grill, Fire Pit, WiFi! features a patio.
  • Parking
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $181.00 Show details »

Double Martini in Oakland, USA

Double Martini

Holiday home in Oakland, Maryland
Situated in Oakland, Double Martini features accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $312.33 Show details »

Clawson Cabin in Oakland, USA

Clawson Cabin

Holiday home in Oakland, Maryland
Located in Oakland, Clawson Cabin provides accommodation with a patio and free WiFi.
  • Parking

no reviews

from $357.67 Show details »

Hideaway in Oakland, USA

Hideaway

Holiday home in Oakland, Maryland
Situated in Oakland, Hideaway features accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $340.68 Show details »

Cozy Alpine Lake Cabin with Pool and Lake Access! in Terra Alta, USA

Cozy Alpine Lake Cabin with Pool and Lak...

Holiday home in Terra Alta near Oakland, Maryland
Set in Terra Alta, Cozy Alpine Lake Cabin with Pool and Lake Access! offers accommodation with a balcony and free WiFi.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $290.33 Show details »

Recreational Therapy in Oakland, USA

Recreational Therapy

Holiday home in Oakland, Maryland
Situated in Oakland, Recreational Therapy features accommodation with a balcony and free WiFi.
  • Parking

no reviews

from $161.67 Show details »

Family-Friendly Terra Alta Home with Lake View! in Terra Alta, USA

Family-Friendly Terra Alta Home with Lak...

Holiday home in Terra Alta near Oakland, Maryland
Featuring a spa bath, Family-Friendly Terra Alta Home with Lake View! is located in Terra Alta.
  • Parking
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $414.33 Show details »

Home Sweet Cabin in Oakland, USA

Home Sweet Cabin

Holiday home in Oakland, Maryland
Set in Oakland, Home Sweet Cabin offers accommodation with a patio and free WiFi.
  • Parking

no reviews

from $313.00 Show details »

Still Meadows in McComas Beach, USA

Still Meadows

Holiday home in McComas Beach near Oakland, Maryland
Still Meadows offers accommodation in Hoyes Run.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • TV
  • Telephone

Exceptional 6 Reviews 9.7

from $266.18 Show details »

Meant to Be in Oakland, USA

Meant to Be

Holiday home in Oakland, Maryland
Located in Oakland, Meant to Be provides accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $333.33 Show details »

Great Escape in Hazelhurst, USA

Great Escape

Holiday home in Hazelhurst near Oakland, Maryland
Set in Hazelhurst, Great Escape offers accommodation with a patio and free WiFi.
  • Parking
  • Tea/Coffee maker
  • TV
  • Telephone
  • Refrigerator

Very good 1 Reviews 8.0

from $272.67 Show details »

Smore Fun in Oakland, USA

Smore Fun

Holiday home in Oakland, Maryland
Boasting a hot tub, Smore Fun is located in Oakland.
  • Parking
  • Pets allowed
  • Indoor pool
  • Outdoor pool
  • Swimming pool

no reviews

from $467.33 Show details »

Poppys Cabin in Oakland, USA

Poppys Cabin

Holiday home in Oakland, Maryland
Poppys Cabin is situated in Oakland.
  • Parking
  • Pets allowed

no reviews

from $144.00 Show details »

Dancing Bears Retreat in Oakland, USA

Dancing Bears Retreat

Holiday home in Oakland, Maryland
Located in Oakland, Dancing Bears Retreat provides accommodation with a patio and free WiFi.
  • Parking

no reviews

from $479.67 Show details »

San-Stress in Oakland, USA

San-Stress

Holiday home in Oakland, Maryland
Situated in Oakland, San-Stress features accommodation with a patio and free WiFi.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $331.67 Show details »

Number of Holiday homes in Oakland 268
Number of guest ratings 1250
Average price per night $384.09
Lowest price per night $120.86
Highest price per night $858.91

Most popular Holiday-homes in Oakland

The most popular Holiday-homes in Oakland based on average guest rating (Top 10).

Cheapest Holiday-homes in Oakland

The cheapest Holiday-homes in Oakland based on room rate per night (Top 10).

Most booked Holiday-homes in Oakland

The most booked Holiday-homes in Oakland based on popularity with guests (Top 10).

Holiday homes in Oakland (Maryland), comfortable and familiar

Staying in a holiday or vacation home in Oakland can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Oakland for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Oakland should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com