
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

Cozy House Surrounded by Nature in Bangor
thank you for such a lovely visit. we had such a great time, we were here for a short night, but the place was great!

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!
This house was perfect for me and my guests! All 7 of us fit perfectly, It didn’t feel too overcrowded! We loved the beautiful view off the deck and the hot tub was an amazing touch! The house was very clean and had everything we could’ve needed. I loved how clear the instructions were for everything and how responsive the hosts are if you need anything!

Peaceful Getaway at The Ledges
Our stay at Margaret's home was very relaxing and comfortable. Pristine bathroom, kitchen and bedding. The lake view was so much more than we anticipated. It was serene, peaceful, and breathtaking. She went out of her way to answer questions for us about the area, and we left feeling like we just gained a new friend. Jeff and Donna

Summer River Retreat with Hiking Trails
By far one of the best Airbnb’s we’ve ever stayed at. Superb location, beautiful river view in front and forest view (with trails) in back. Plenty of garden space to run around in with the kid(s). And only a 5-minute drive into quaint and charming Bath. The place itself was beautifully laid out, with so much space and comfort. Pip was always available, efficient and kind and to communicate with. Cannot recommend this place enough if you’re looking respite in nature, comfort in home, and proximity to town.

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!!

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!
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!
What a wonderful experience! Rebecca was an absolutely outstanding host, always quick to respond and went above and beyond to ensure we had everything we needed. My family and I had such a peaceful stay. The home and location were incredibly tranquil, perfect for a relaxing getaway. The house and property were absolutely beautiful, and we loved sipping our morning coffee on the amazing balconies with the breathtaking views. There is so much space, and every room in the house is well thought out, functional, and cozy. The pool is even better than we hoped, so big and clean and in immaculate condition. We spent most of our time swimming and relaxing by the pool. We also enjoyed playing pool and having so many rooms to gather in with the comfort of plenty of new comfy furniture. Highly recommend for anyone looking to unwind for a vacation away from all the noise and chaos of daily life. Every single area was as described in the listing and better. Thank you for an unforgettable stay!

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.

Riverfront Luxury in the woods, Million $ Views.
Property had amazing views. Inside was beautiful and very clean. Pond and river was nice. Host was quick with any question we had. would recommend.10/10

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.
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!

Classy AF Home, walk across the street to Colby!
The photos don’t do this place justice! It is extremely pretty and bigger than I thought! Its location is perfect and made for an easy reunion weekend at Colby!

Lakefront cottage in Belgrade Lakes
Jennifer was great - had a few questions and her responses were near immediate. The place is as described- simple but comfortable and cozy for a family of 4. It rained so I cant comment on the lake activities but the fenced in yard was perfect for the dogs and a beautiful spot. hoping to go back in the summer when weather is better. Definitely recommend if you are looking for a getaway and like simplicity.

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.

Raccoon Suite
Lance was very responsive, helpful and friendly. The apartment is lovely and was just what I needed.
Quick stats about holiday rentals that are pet-friendly in Oakland
Total rentals
20 properties
Nightly prices starting at
₹5,165 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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- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- Saddleback Ski Mountain Maine
- Belgrade Lakes Golf Club
- Sugarloaf Golf Club
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Rockland Breakwater Light
- Eaton Mountain Ski Resort
- Pinnacle Park
- Spragues Beach
- Lost Valley Ski Area
- Pebble Beach
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach
- Black Mountain of Maine
- Farnsworth Art Museum
- The Camden Snow Bowl
- Martindale Country Club