Book a Dog-Friendly Rental in Oakland for Your Next Adventure
About Oakland Pet Friendly Vacation Rentals on Vacation Cottage
Traveling with your pet? With more than 275 luxurious and picturesque oceanfront resorts, hotels, and rentals in or near Oakland? Vacation Cottage features some truly exceptional places to stay. Whether you are traveling with groups, families, friends, or as a couple to Oakland, our options provide maximum comfort and scenic views. Many of our luxury destinations welcome pets and offer essential amenities such as full kitchens, Wi-Fi, hot tubs, outdoor pools, recreation and theater rooms, laundry facilities, and more, providing the perfect place to unwind.
Looking for a beach or oceanfront rental that welcomes dogs in Oakland, Maryland? Vacation Cottage has a large selection of pet-friendly villas, condos, cabins, and cottages, as well as boutique hotels and luxury resorts. Our rentals cater to both large and small travel groups. Let Vacation Cottage vacation homes assist you in finding the perfect luxury accommodation for you and your pet in Oakland that meets your travel budgets and desires, offering direct access to stunning beaches and ocean views. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Oakland Pet-Friendly Rentals
What are the top rated Pet Friendly Vacation Rentals in Oakland?
There are a lot of options in Oakland. If you plan on staying in the Oakland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Pet Friendly Vacation Rentals in Oakland:
- Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
- The Love Shack- The BEST Couples and Small Family Retreat at Deep Creek Lake!
- Sunny Escape 2 - A new era for a familiar lake front home
- Lakefront, dog friendly, dock slip, hot tub, and fire pit
- Unobstructed lake views from living areas. Restaurants & activities in minutes
- Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
- Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
- The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
- That Special Place
- La Bella Vita | Amazing Lake Views, Upscale Decor
How many pet-friendly vacation rentals are available in Oakland on Vacation Cottage?
There are more than 275 pet-friendly rentals available on Vacation Cottage. Check prices and availability in Oakland and last updated on October 2025. Check an individual property if they have restrictions on the size or numbers of pets.
Which is the best dog-friendly place to stay in Oakland?
There are many dog-friendly vacation homes available in Oakland. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Oakland:
- Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
- Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr
- Mountain House
- The Love Shack- The BEST Couples and Small Family Retreat at Deep Creek Lake!
Do you have any luxury vacation homes that allow pets in or near Oakland?
Most definitely! There are many luxury places to stay in Oakland. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Oakland. Though note, more expensive is not always better.
What is the price of a pet-friendly rental in Oakland, Maryland?
The average price of a pet-friendly vacation home is $484. Find our pet-friendly accommodation near Oakland.
What are the most family-friendly holiday rentals near Oakland?
At Vacation Cottage, many of our accommodations are perfect for families and allow dogs too. Check out the complete list of pet-friendly holiday rentals in Oakland to find what works for you.
