Pet Friendly Hotels in Oakland, MD

There are 87 pet friendly hotels in Oakland. Need help to decide where to stay with your dog? You can browse the results below and filter by amenities to find the perfect spot. BringFido members never pay a booking fee, and their reservations are backed by our Pet Friendly Guarantee!

$317

No pet fee

Big dogs OK

2+ pets OK

Sleeps 10

Cedar Ridge

4.5 Oakland, MD

Cedar Ridge Pet Policy This 3-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$484

No pet fee

Big dogs OK

2+ pets OK

Sleeps 14

Boxer Overlook

4.7 Oakland, MD

Boxer Overlook Pet Policy This 5-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$99+

No pet fee

Big dogs OK

2+ pets OK

Pet-Friendly Airbnb Rentals

Oakland, MD

$673

No pet fee

Big dogs OK

2+ pets OK

Sleeps 14

American Pride

4.7 Oakland, MD

American Pride Pet Policy This 5-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$318

No pet fee

Big dogs OK

2 pets max

Sleeps 6

The Whitetail

4.8 Oakland, MD

The Whitetail Pet Policy This 2-bedroom cabin in Oakland allows 2 dogs of any size for no additional fee. Breed restrictions apply. Pets must be approved in advance. Sorry, no cats or excessive barking. Dogs must be current on all vaccinations and flea & tick medication. Please leash and clean up after your pets on the property. Visit Website

$708

No pet fee

Big dogs OK

2+ pets OK

Sleeps 16

Innisfree

4.8 Oakland, MD

Innisfree Pet Policy This 5-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$1 019

No pet fee

Big dogs OK

2+ pets OK

Sleeps 18

St. Bart's Retreat

4.5 Oakland, MD

St. Bart's Retreat Pet Policy This 7-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$333

No pet fee

Big dogs OK

2+ pets OK

Sleeps 10

Heart and Soul

4.7 Oakland, MD

Heart and Soul Pet Policy This 4-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$338

No pet fee

Big dogs OK

2+ pets OK

Sleeps 10

The Perch

4.8 Oakland, MD

The Perch Pet Policy This 3-bedroom vacation rental in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$400

No pet fee

Big dogs OK

2+ pets OK

Sleeps 8

Lakeview Cottage

4.5 Oakland, MD

Lakeview Cottage Pet Policy This 3-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$365

No pet fee

Big dogs OK

2+ pets OK

Sleeps 6

Beautiful Adventure

4.7 Oakland, MD

Beautiful Adventure Pet Policy This 3-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$1 069

No pet fee

Big dogs OK

2+ pets OK

Sleeps 18

Friday's Escape

4.5 Oakland, MD

Friday's Escape Pet Policy This 7-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$432

No pet fee

Big dogs OK

2+ pets OK

Sleeps 12

Picture Perfect

4.8 Oakland, MD

Picture Perfect Pet Policy This 4-bedroom vacation rental in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$542

No pet fee

Big dogs OK

2+ pets OK

Sleeps 16

Fancy Free

4.6 Oakland, MD

Fancy Free Pet Policy This 4-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$750

No pet fee

Big dogs OK

2+ pets OK

Sleeps 12

Black Bear Lodge

5.0 Oakland, MD

Black Bear Lodge Pet Policy This 4-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$415

No pet fee

Big dogs OK

2+ pets OK

Sleeps 10

180 Degrees

4.5 Oakland, MD

180 Degrees Pet Policy This 3-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$357

No pet fee

Big dogs OK

2+ pets OK

Sleeps 8

Hideaway

4.4 Oakland, MD

Hideaway Pet Policy This 2-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website

$901

No pet fee

Big dogs OK

2 pets max

Sleeps 20

Waterfront Chateau

4.7 Oakland, MD

Waterfront Chateau Pet Policy This 7-bedroom house in Oakland allows 2 dogs of any size for no additional fee. Breed restrictions apply. Pets must be approved in advance. Sorry, no cats or excessive barking. Dogs must be current on all vaccinations and flea & tick medication. Please leash and clean up after your pets on the property. Visit Website

$318

No pet fee

Big dogs OK

2 pets max

Sleeps 8

Linwood

4.6 Oakland, MD

Linwood Pet Policy This 3-bedroom house in Oakland allows 2 dogs of any size for no additional fee. Breed restrictions apply. Pets must be approved in advance. Sorry, no cats or excessive barking. Dogs must be current on all vaccinations and flea & tick medication. Please leash and clean up after your pets on the property. Visit Website

$357

No pet fee

Big dogs OK

2+ pets OK

Sleeps 8

Retro Lake Landing

4.1 Oakland, MD

Retro Lake Landing Pet Policy This 3-bedroom house in Oakland is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website