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Holiday homes in Oakland You’ll Love

Top-Rated Oakland Holiday homes for Every Budget and Style!

Looking for a holiday home in Oakland (Maryland)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Oakland.

We found 13 Holiday-homes in Oakland and the surrounding area (within 40 miles)

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
With free Wifi, this 3-bedroom vacation home provides a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave.
  • Parking
  • Pets allowed

Superb 3 Reviews 9.3

from $73.00 Show details »

Windy Acres in Oakland, USA

Windy Acres

Holiday home in Oakland, Maryland , 493 Herrington Manor Road
Both free Wifi and parking on-site are available at Windy Acres free of charge.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 1 Reviews 10.0

from $231.09 Show details »

New Construction Beautiful Lake Front and Beautiful Home in Oakland, USA

New Construction Beautiful Lake Front an...

Holiday home in Oakland, Maryland , 763 Chadderton School Road
The vacation home also includes a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as a hair dryer.
  • Parking

no reviews

from $1.655.99 Show details »

Hot Tub and Dogs Welcome Secluded Oakland Gem in Oakland, USA

Hot Tub and Dogs Welcome Secluded Oaklan...

Holiday home in Oakland, Maryland
With free Wifi, this 3-bedroom vacation home provides a cable flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and ov...
  • Parking
  • Pets allowed
  • Spa and wellness centre

no reviews

from $284.19 Show details »

Private Lake Beach Cabin w Golf Pool Fire pit in Terra Alta, USA

Private Lake Beach Cabin w Golf Pool Fir...

Holiday home in Terra Alta near Oakland, Maryland , East Alpine Drive 479
Featuring a garden, Private Lake Beach Cabin w Golf Pool Fire pit features accommodations in Terra Alta.
  • Parking
  • Pets allowed

Very good 2 Reviews 8.5

from $175.60 Show details »

Woodland Sage in Oakland, USA

Woodland Sage

Holiday home in Oakland, Maryland , 426 Pergin Farm Road
This vacation home provides free private parking and free Wifi.
  • Parking
  • Pets allowed

no reviews

from $52.00 Show details »

The Bears Den Lodge in Terra Alta, USA

The Bears Den Lodge

Holiday home in Terra Alta near Oakland, Maryland , 278 Goldenrod Drive
Offering barbecue facilities, The Bears Den Lodge features accommodations in Terra Alta.
  • Parking
  • Restaurant
  • Pets allowed
  • Family rooms
  • Indoor pool

Exceptional 6 Reviews 9.6

from $99.00 Show details »

Millstone Cottage at Alpine Lake Resort in Terra Alta, USA

Millstone Cottage at Alpine Lake Resort

Holiday home in Terra Alta near Oakland, Maryland , 654 Primrose Lane
This property offers access to a patio and free private parking.
  • Parking
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $63.00 Show details »

Swallow Falls Cabin 1 in Oakland, USA

Swallow Falls Cabin 1

Holiday home in Oakland, Maryland , 1691 Swallow Falls Road DCL01
Guests staying at this vacation home have access to free Wifi.

no reviews

from $157.66 Show details »

Swallow Falls Cabin 2 in Oakland, USA

Swallow Falls Cabin 2

Holiday home in Oakland, Maryland , 1691 Swallow Falls Road DCL02
Guests staying at this vacation home have access to free Wifi.

Good 1 Reviews 7.0

from $162.22 Show details »

Swallow Falls Cabin 3 in Oakland, USA

Swallow Falls Cabin 3

Holiday home in Oakland, Maryland , 1691 Swallow Falls Road DCL03
Guests staying at this vacation home have access to free Wifi.

Poor 2 Reviews 3.5

from $178.86 Show details »

Swallow Falls Cabin 4 in Oakland, USA

Swallow Falls Cabin 4

Holiday home in Oakland, Maryland , 1691 Swallow Falls Road DCL04
Guests staying at this vacation home have access to free Wifi.

Exceptional 1 Reviews 10.0

from $185.93 Show details »

Serenity Chalet in Oakland, USA

Serenity Chalet

Holiday home in Oakland, Maryland , 330 Red Run Heights
With free Wifi, this 3-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $331.56 Show details »

Number of Holiday homes in Oakland 13
Number of guest ratings 813
Average price per night $352.00
Lowest price per night $50,00
Highest price per night $2.774,18

Top 10 Cheapest Holiday-homes in Oakland

Discover the Cheapest Holiday-homes in Oakland – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Oakland

Check out the Most Booked Holiday-homes in Oakland – Based on Guest Popularity.

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