
Pet-friendly vacation rentals in Oakland
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Top-rated pet-friendly home rentals in Oakland
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Popular amenities for Oakland pet-friendly home rentals
Pet-friendly house rentals

Sunny 2-BR 5 min to Bates & River Trails
This is the 2nd time I've stayed at Emma's place. I came both times for a workshop and ceremony that took place in both Freeport and in Portland. Drives to Portland were the longest, and not too taking, and I chose to stay at Emma's place BECAUSE of the way the house holds me: the spaciousness, the attention to art and wisdom, the lighting and unfussy-yet-design-inspired furniture choices, the plant life, the textures and colors: all these things are soothing and welcoming. It was a pleasure to drive "home" exhausted, knowing what it feels like to open that back door.

Summer River Retreat with Hiking Trails
Everything was as described! Very tranquil setting. Loved sitting on both the sunporch and deck watching the boats go by. The house was immaculate and very well equipped. NIce to relax without the distraction of tv for a change. Enjoyed their Bose radio.. Also the verizon phone /computer connection was excellent. It was a great home base for exploring the mid coast of Maine. Lots of good restaurants near by and the owner offered many heloful hints as to what to see, where to est and what to do. His communication was excellent. Would highly recommend this rental.

The Riverfront Retreat - 27 minutes to Sugarloaf!
Great little cozy spot, clean, lots of plants and lights. Very comfortable. Nice little spot on the property by the stream. Close to a variety of hikes and waterfalls. Very happy with our stay.

Riverside
This was my 5th time going there and I love it! The house is so cozy & very clean. The property is large and the view is breathtaking over looking the river. They are also pet friendly so we were able to take our Lhasa Apso Revy on vacation with us. Besides how great this Air BnB is, my favorite is the hosts Kent & Tish! They are wonderful people. They are kind & friendly, & have such beautiful souls. They have become family to me! I highly recommend getting this air bnb!! Thank you again Tish & Kent! Ian, Revy, & I are always happy to see you!!

The Strawberry House
The Strawberry house was such an amazing place for my wife and I to spend our first anniversary. We go to midcoast Maine every year and this was certainly a special one for us. Comfortable, thoughtfully designed and accessible to town. Highly recommend!

Lakefront Log Cabin on Pleasant Lake
The lakeside cabin was just what I needed. Quiet, private, and right on the water. My dog loved running in the yard and swimming in the lake. The cabin was comfortable with all the basics, and sitting on the porch watching the water was so relaxing. Perfect spot to unwind and enjoy some peace and quiet.

Rustic Farmhouse at Oxbow Brewery
My husband and in-laws and I and our two dogs stayed for a long MDW. The weather did not cooperate but did not hinder us. Especially staying at this Airbnb on the beautiful Oxbow Brewing property. In fact the coziness of the space made a rainy day even more fun. We were visiting for the racetrack and location was excellent for privacy and also close to local attractions. Wish we had more of a group to experience the space with us, it was really special!

Quiet 2 bedroom home, snowmobile from property.
Beautiful place to stay nearby a picturesque river and close to skiing. Michael is a communicative and accommodating host. Kingfield is a charming town. We appreciated that they had cable as well – rare for an AirBNB.
Pet-friendly home rentals with a pool

Large Home with Great View next to horse farm
Beautiful and peaceful place! Just admiring the surroundings let the peace and tranquility set in and consume you. Highly recommend! Teresa is a wonderful host and flexible to your needs. Will definitely visit again, thank you Teresa!

Luxe Liberty: Getaway with Heated Indoor Pool!
this was the 3rd time our family has stayed,again we had a fantastic time! We chose to return due to the great space, a fabulous indoor pool, great kitchen and an amazing view. Great attention to details, comfortable for large families or groups and peaceful for just 2.

Lovely home with hot tub and pool
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

Mercer Apartment in the Valley-Peaceful Country
I stayed there for two weeks and I would stay again. It was very quiet which is my number one need. Two it was clean. Three nice kitchen with all the appliances you need. Four Jeanmarie answered all questions quickly and clearly. Five lots of room in the house. Six it was nice and warm in the winter weather.

Lawn Cottage - Newly Renovated 2024
Adorable cottage, newly renovated. Perfect for two with an open space loft for one more. Kitchen is well stocked right down to the coffee. A good location if visiting Fort Knox, Mt. Barrie and not too far from Bar Harbor if that is on your list. Great stay, highly recommend. Beautiful view and private.

Cozy Chalet, 10-Min Drive to Sugarloaf, Sleeps 9
Had an awesome stay at Mathews place. 20 min drive from Sugarloaf with an option for a shuttle even. Cozy spot next to a beautiful river. Allowed us to check out an hour late.

A place to be The Hidden Gem Mt Vernon, Me
The host gave us an upgrade to another tiny house in the same location that we gladly accepted. We were welcomed by fresh lilacs in the tiny home with cozy ambiance. The location is remote with a small farm stand (the honey from this stand is a must, we got the biggest jar and we have zero regrets). This is a peaceful retreat with beautiful views and hikes. I recommend this to anyone looking to escape the city.

Cozy Apartment with In-Town Convenience
I had a great month exploring Maine with my dog from this garage apartment. The owners are friendly but not intrusive. Some days my dog and I just laid a blanket on the grass and sat in the beautiful backyard. Go to Pickles Potions and get the body oil, it helped me keep bugs away.
Private, pet-friendly home rentals

Bear Cub Lodge
Erin & Joseph were the BEST hosts! Booked before they were superhosts and honestly, they deserve it! Full kitchen. Cabin smells so amazing — like fresh lumber. Reminds me of my grandfather’s cottage from my childhood. There’s a fire pit which was perfect for our stay. Bed was super comfortable! We came for our anniversary and they left us water bottles, flowers, mugs, cake and cookies — which were SO GOOD! There was also movie snacks waiting for us on the coffee table! It’s so peaceful, we hated to leave. The natural lighting makes the morning sunlight come into the cabin so lovely. It was an absolute dream! There are also board games upstairs for kiddos! There’s also a trail to walk around in the woods. There’s tons of parking. If you like supporting local businesses, there’s plenty around for firewood, honey, pastries, syrup, etc. Erin was also so sweet when we forgot to take the trash out for checking out 🤦🏻♀️😆 Seriously, book with them! It was the best AirBnB experience we’ve ever had

Private tiny cabin on six acres of trees
The hosts are extremely kind and the cabin is perfect for a nice getaway.. we had a lot of fun and enjoyed the trails, and our cat loved his time there as well. The firepit outside was perfect for roasting marshmallows and making smores, and we’re hoping to come back again.

New Cozy Rustic Cabin on 58 private acres
lovely spot, everything you need for a nice getaway

Upstairs apartment
10-10 would recommend anytime great place to stay

Cozy Lakefront Retreat
Great trip! Great hosts! Very peaceful!

Entire 3 BR apartment in Winslow
The interior space looked just as described. It was clean and it appears that Anima did some work to make it more updated. I slept comfortably and that was most important. The outside of the house could use a little TLC. This was my first time visiting Maine; I was not sure what to expect. Anima is kind and very responsive to messaging. I would definitely stay in any space that she offered in the future.

Camp at Shale Creek Homestead
Their family were extremely welcoming to our family. We loved seeing their extremely friendly cats, as well as their goats and chickens, and the RV was comfortable and clean. We would definitely recommend this place to stay if you’re in the area!!

Lakefront apartment near Western Maine mountains
We had a wonderful stay! Lisa is very responsive and so nice. We quickly made friends with Bella, the resident dog, and she is the sweetest pup. We were surprised with a Thanksgiving snow storm and the town lost power but there is a whole house generator, so we didn’t skip a beat or notice the power outage, which was so nice! There is a coffee pot on site (not a Keurig) and Lisa provided coffee grounds, which was amazing because we brought coffee pods. The bathroom is directly off the bedroom but there is no door, so if you need more privacy, I’d plan to tack up a blanket. The view of the lake is gorgeous and the property is peaceful. A gas station with a Dunkin is just a just a minute or two down the road and very convenient. We would definitely return.
Quick stats about vacation rentals that are pet-friendly in Oakland
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
840 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Saddleback Ski Mountain Maine
- Sugarloaf Golf Club
- Maine Maritime Museum
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Three Island Beach
- Rockland Breakwater Light
- Spragues Beach
- Eaton Mountain Ski Resort
- Pinnacle Park
- The Camden Snow Bowl
- Bear Island Beach
- Narrow Place Beach
- Lost Valley Ski Area
- Pebble Beach
- Black Mountain of Maine
- North Point Beach
- Martindale Country Club