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Holiday homes in Oakland (Page 9)

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)
Main Street Retreat in McHenry, USA

Main Street Retreat

Holiday home in McHenry near Oakland, Maryland
Set in McHenry, Main Street Retreat offers accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $374.50 Show details »

Oak View Ridge in Swanton, USA

Oak View Ridge

Holiday home in Swanton near Oakland, Maryland
Set in Swanton, Oak View Ridge offers accommodation with a patio and free WiFi.
  • Parking

no reviews

from $225.71 Show details »

Top of the Slopes in McHenry, USA

Top of the Slopes

Holiday home in McHenry near Oakland, Maryland
Located in McHenry in the Maryland region, Top of the Slopes features a balcony and mountain views.
  • Parking

Superb 9 Reviews 9.1

from $379.29 Show details »

Cabin at Slopes Edge in McHenry, USA

Cabin at Slopes Edge

Holiday home in McHenry near Oakland, Maryland
Set in McHenry, Cabin at Slopes Edge offers accommodation with a patio and free WiFi.
  • Parking

no reviews

from $271.00 Show details »

Piney Bear Cabin in Swanton, USA

Piney Bear Cabin

Holiday home in Swanton near Oakland, Maryland
Featuring a hot tub, Piney Bear Cabin is situated in Swanton.
  • Parking

no reviews

from $201.67 Show details »

At Ease in Swanton, USA

At Ease

Holiday home in Swanton near Oakland, Maryland
Located in Swanton, At Ease provides accommodation with a balcony and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $401.67 Show details »

Hillside Hideaway in McHenry, USA

Hillside Hideaway

Holiday home in McHenry near Oakland, Maryland
Hillside Hideaway is situated in McHenry.
  • Parking

Very good 6 Reviews 8.0

from $178.67 Show details »

Little Bear in McHenry, USA

Little Bear

Holiday home in McHenry near Oakland, Maryland
Boasting a hot tub, Little Bear is located in McHenry.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $498.67 Show details »

18 Winding Way in McHenry, USA

18 Winding Way

Holiday home in McHenry near Oakland, Maryland
18 Winding Way is set in McHenry.
  • Parking
  • Tea/Coffee maker
  • Shower
  • Bath
  • TV

Very good 12 Reviews 8.3

from $338.26 Show details »

VOW Winding Way 11 in McHenry, USA

VOW Winding Way 11

Holiday home in McHenry near Oakland, Maryland
VOW Winding Way 11 offers accommodation in McHenry.
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • TV
  • Telephone

Good 5 Reviews 7.4

from $234.00 Show details »

Bear's Den in McHenry, USA

Bear's Den

Holiday home in McHenry near Oakland, Maryland
Featuring a hot tub, Bears Den is located in McHenry.
  • Parking
  • Tea/Coffee maker
  • TV
  • Hot tub
  • Balcony

Pleasant 6 Reviews 6.8

from $198.33 Show details »

Winding Down Slope Side in McHenry, USA

Winding Down Slope Side

Holiday home in McHenry near Oakland, Maryland
Situated in McHenry, Winding Down Slope Side features accommodation with a balcony and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $263.38 Show details »

Bear Mountain Lodge in Swanton, USA

Bear Mountain Lodge

Holiday home in Swanton near Oakland, Maryland
Set in Swanton, Bear Mountain Lodge offers accommodation with a patio and free WiFi.
  • Parking
  • Fitness centre

no reviews

from $336.13 Show details »

Cedar Shores Villa 12 in McHenry, USA

Cedar Shores Villa 12

Holiday home in McHenry near Oakland, Maryland
Situated in McHenry, Cedar Shores Villa 12 features accommodation with a patio and free WiFi.
  • Parking

no reviews

from $349.68 Show details »

Sunrise Cove in McHenry, USA

Sunrise Cove

Holiday home in McHenry near Oakland, Maryland
Featuring a hot tub, Sunrise Cove is situated in McHenry.
  • Parking
  • Pets allowed

no reviews

from $464.67 Show details »

Cedar Shores Villa 08 in McHenry, USA

Cedar Shores Villa 08

Holiday home in McHenry near Oakland, Maryland
Boasting a hot tub, Cedar Shores Villa 08 is located in McHenry.
  • Parking
  • Fitness centre

no reviews

from $266.67 Show details »

Waters Edge in McHenry, USA

Waters Edge

Holiday home in McHenry near Oakland, Maryland
Offering free WiFi and mountain views, Waters Edge is an accommodation situated in McHenry.
  • Parking
  • Pets allowed

no reviews

from $395.23 Show details »

Simpsons Sanctuary in McHenry, USA

Simpsons Sanctuary

Holiday home in McHenry near Oakland, Maryland
Boasting a hot tub, Simpsons Sanctuary is located in McHenry.
  • Parking
  • Pets allowed

no reviews

from $383.25 Show details »

Bourbon Sunsets in McHenry, USA

Bourbon Sunsets

Holiday home in McHenry near Oakland, Maryland
Set in McHenry, Bourbon Sunsets offers accommodation with a patio and free WiFi.
  • Parking

no reviews

from $401.67 Show details »

Captains Cove in Swanton, USA

Captains Cove

Holiday home in Swanton near Oakland, Maryland
Captains Cove is located in Swanton.
  • Parking

no reviews

from $332.85 Show details »

Happy Landing in McHenry, USA

Happy Landing

Holiday home in McHenry near Oakland, Maryland
Set in McHenry, Happy Landing offers accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $392.00 Show details »

Suite Sunsets in McHenry, USA

Suite Sunsets

Holiday home in McHenry near Oakland, Maryland
Situated in McHenry, Suite Sunsets features air-conditioned accommodation with a patio and free WiFi.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $414.57 Show details »

Sunplace 07 in McHenry, USA

Sunplace 07

Holiday home in McHenry near Oakland, Maryland
Situated in McHenry, Sunplace 07 features accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed
  • Indoor pool
  • Outdoor pool
  • Swimming pool

no reviews

from $279.00 Show details »

Livin Lodge in McHenry, USA

Livin Lodge

Holiday home in McHenry near Oakland, Maryland
Livin Lodge is set in McHenry.
  • Parking

no reviews

from $348.89 Show details »

Solitude in Swanton, USA

Solitude

Holiday home in Swanton near Oakland, Maryland
Located in Swanton, Solitude provides accommodation with a patio and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $413.78 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