
Pet-friendly holiday 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

Sugarmaple Lakehouse - Sebasticook Lake Newport ME
Enjoyed a wonderful weekend here with our family (5 adults, 1 child, 1 dog). The house is very comfortable & beautifully updated/decorated. The setting is even better in person than we were expecting with an expansive lawn perfect for playing games. We had read other reviews about the neighbors having free roaming pet rabbits and saw them quite a bit. Fortunately our dog is a good listener and left them alone but could prove challenging for other dogs depending on their temperament. The lake was gorgeous and the location within one of the coves felt quiet and private while offering easy access to the rest of the lake via boat, kayak, etc. Enjoyed sitting on the dock & picnic table by the waters edge. Appreciated all the kayaks, games, toiletries & kitchen items provided as well as the large deck with grill & the firepit with chairs. Conveniently close to the boat launch, grocery store, restaurants, gas station, etc. if you need to run out for anything. Thanks for a great stay!

Spectacular 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
This cabin is perfect for a peaceful Maine getaway. Tucked right on the water’s edge, the views are absolutely breathtaking. The cabin itself is cozy. We loved having morning coffee on the dock and taking out the row boat provided. My dog enjoyed being able to swim in the lake. Devon was incredibly welcoming and responsive. If you're looking for a quiet, rejuvenating escape with unbeatable lakefront access, this is it. We can’t wait to come back next season!

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!

Cedar Swamp Farm
We had a great stay! This is a lovely private spot and the horses were definitely a plus! We would definitely like to stay here again.
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!

A+ Views -Jet Spa Tub Sauna Sunset/Stars
Jonathan and Lisa were wonderful hosts! We stayed 3 nights to enjoy some Spring skiing at Saddleback. The home was close to town and a quick drive to Saddleback mountain. The house is perched high on a hill overlooking Rangeley lake. The downside is that the driveway is steep and icy (this time of year due to the recent March thaws) but the view and sunsets are breathtaking!! For an additional fee, you can enjoy their newly built sauna and whirlpool. So relaxing after a day of skiing that we booked it twice. The house has all the comforts of home. Being culinary masters, we had a bit of a struggle in the small kitchen. But certainly most everything you need to prepare great meals. Communication with the hosts was excellent and timely.

Luxe Liberty: Getaway with Heated Indoor Pool!
This was one of the most memorable places I have ever lived at! The property is huge, well maintained and just a perfect getaway spot with the right amount of amenities. Will definitely recommend this place 10/10 to anyone visiting Acadia National Park.

Lovely home with hot tub and pool
I had a wonderful stay., they were fantastic in accommodations for me and my service dog who loved the yard. The home is beautiful and the host was very accommodating. communication was great. I look forward to staying there when I’m in that area again.

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.

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

epicurean feast with zen like surroundings
Brenda’s place was everything we’d hoped for and more! The cottage was clean and comfy, and surrounded by so many gigantic, gorgeous trees. Brenda’s cooking and hospitality were a huge highlight! She gave excellent local recommendations and cooked us two delicious meals. Our dog was in heaven. Would absolutely come back!

In the heart of Augusta 1 Bedroom
Your place was perfect for our intern. It was clean and safe!

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.

Cozy Lakefront Retreat
Absolutely wonderful time, couldn't ask for better hosts!! The special touches were so welcoming!! We had Flowers, & s'more fixings waiting for us 😊 The bedding smelt so fresh & clean!! It was perfect!! The lake was breathtaking 😍 we enjoyed being able to kayak & paddle boat. They even left us wood for a fire. The kitchen had everything we needed & then some !! I could go on & on !!! I'd recommend to anyone looking to unplug & just relax! I'd love to go again! Thank you 💙

Camp at Shale Creek Homestead
Loved, loved, loved our stay in Patrick’s camper! Everything was as described. We totally relaxed and slept like rocks! The bed was great! We cooked our own supper on the little stove and watched some Gunsmoke on the TV that had tons of channels!! We opened up the windows and it was so comfortable! We loved being near the goats and chickens! The little Lori’s Cafe in nearby Liberty, ME is soooo gooood!! We would go back in a second! Thanks, Patrick!!

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.

Lakefront apartment near Western Maine mountains
Lisa is a great host, and her place is very comfortable. I stayed a couple months with my dog while working in the area, and she was very accommodating. I would not hesitate to book her place again if ever in the area.

Super cute waterfront cottage
10/10 would recommend for a gorgeous, peaceful retreat in Maine. Calvin and Christine were excellent hosts - great recommendations and very very responsive. The home offers beautiful natural light, good amenities and isn’t too far from the main town. The view of the water is absolutely incredible especially when you go down to the dock. We ended up enjoying most of our meals at the house and the kitchen was well-equipped for easy meal prep. If we’re ever in the area again would definitely rebook!
Quick stats about holiday rentals that are pet-friendly in Oakland
Total rentals
20 properties
Nightly prices starting at
$77 SGD 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
- Rockland Breakwater Light
- Three Island Beach
- Pinnacle Park
- Eaton Mountain Ski Resort
- Spragues Beach
- Narrow Place Beach
- Lost Valley Ski Area
- Bear Island Beach
- The Camden Snow Bowl
- Pebble Beach
- Black Mountain of Maine
- Martindale Country Club
- Farnsworth Art Museum