Dog-friendly vacation rentals in Oakland

We found 13 vacation rentals waiting for you.

Furry friends and wagging tails welcome

Oakland is even more fun with your four-legged friends. Discover pet-friendly vacation homes with amenities your pup will love, like large outdoor spaces to play and cozy nooks for napping.

Top-rated dog-friendly rentals in Oakland

Pet parents have spoken. Explore some of their favorite dog-friendly homes in Oakland, offering the perfect blend of relaxation and adventure for your pup.

Woodsy Way Cabin
2 Bed | 2 Bath | Sleeps 9

Woodsy Way Cabin - Oakland, MD

From $170
(excludes fees and taxes)
4.54 (39)
Great Escape
2 Bed | 2 Bath | Sleeps 10

Great Escape - Oakland, MD

From $320
(excludes fees and taxes)
4.0 (75)
Nimba Cabin
3 Bed | 3.5 Bath | Sleeps 10

Nimba Cabin - Oakland, MD

From $229
(excludes fees and taxes)
3.88 (8)
Oakland Oasis
2 Bed | 2 Bath | Sleeps 4

Oakland Oasis - Oakland, MD

From $152
(excludes fees and taxes)
5.0 (2)

Explore All Dog-friendly Vacation Rentals

Recent guest reviews

Have to concur with some of the reviews regarding the cleanliness of the back deck and the poor Internet connection. That said, once you sweep the back deck yourself and realize that you should be out on the lake instead of surfing the web, you start to look past the imperfections. One of the best family vacations that I can remember.
Bradley B. | Jul 2025
So many nice amenities to be comfortable for a week at a cabin in the woods, air conditioning and wifi. Many nearby trails and the private community property for nature appreciation activities.
Dara K. | Jul 2025
The cabin offers a perfect getaway for a couple or a couple of families! We enjoyed the spacious deck for grilling and eating meals outside. The hot tub was beautifully maintained and great way to end each evening. There is plenty of seating areas both inside and outside and the fire pit area it lit so beautifully with strung bulb lights. The cabin was well stocked with towels and basic essentials. If you are looking for a great place to enjoy family, friends or even a personal retreat, this is the place!! We spent time at deep creek lake during the day, Swallow Falls for hiking and Wisp Adventure Sports. All about 20 minutes away! We look forward coming back to this cabin.
Jenny K. | Jul 2025
Very spacious, kids loved the pool table, great location to beach, restaurants and activities.
Amanda P. | Jun 2025
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Pet policies apply

FAQ

Yes, a pet fee is charged at all of our pet-friendly vacation rentals. No deposit is required. The amount varies depending on the property’s location, size, and helps to cover extra cleaning procedures.

Dogs are the only type of animals allowed in our pet-friendly vacation homes. As required by law, we also allow service animals in our vacation rentals.

Weight limits and the number of dogs allowed vary by home; any limits will be clearly stated in the description of each listing.

Le nombre d'animaux autorisés par location dépend de la taille de la maison, des préférences du propriétaire et des restrictions de la communauté ou de l'association de propriétaires. Le nombre d'animaux autorisés est indiqué dans la description de l'annonce.

Some homes offer designated pet relief areas on the property. We recommend checking the property description or contacting us for details.

Pet waste bags are not usually provided (though some homes do offer these as a perk), so it is best to bring your own.

Rules concerning dogs are always changing. We suggest going to the official city website, where you’ll often find a list of any regulations, leash laws, and other relevant information. In addition, certain homeowners' associations have restrictions regarding pets.

Pet food and water bowls are not usually provided (though some homes do offer these as a perk), so it is best to bring your own.

Dog towels are not usually offered at pet-friendly vacation homes (though some homes may offer them as an extra amenity), so it is best to bring your own.

Dogs are not usually allowed on the furniture in vacation rentals. We recommend bringing your pet's favorite blanket or bed to lie on.

More ways to stay in Oakland

Hot tub
Internet
Pool
Electric vehicle charger
Lake view
Lakefront
Ski-in/ski-out
Sound view

Nearby destinations

Appalachian Mountains
Western Maryland
Deep Creek Lake
Swanton
McHenry
Kitzmiller
Accident
Bittinger
USA > Maryland > Oakland > Dog-friendly

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