
Waterfront holiday rentals in Oakland
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Top-rated waterfront rentals in Oakland
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Waterfront apartment rentals

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!

Stunning Royal Richmond 2 Br Apartment Get Away!
We are so grateful for our stay at Alice's place. My husband and I stayed with our two small daughters and had a blast. The apartment was so beautiful- updated but with lots of attention to detail and Maine character. We especially enjoyed meals in the little dine in kitchen, and having laundry available. I was familiar with this area as a former Mainer, and the quiet neighborhood made us feel at home. Thank you so much! We highly recommend Alice's place. :)

Downtown waterfront Belfast with amazing views.
We had a lovely stay at the Downtown Harbor apartment in the middle of June. The view is beautiful and the apartment is attractive, clean, and comfortably furnished. Larry and Sharon were extremely accommodating and really cared about our experience. Highly recommended to singles and couples visiting this part of the Maine coast.

Sail Loft - Upscale Oceanfront on a Pier near BBH!
Pam's place was absolutely perfect. The location was ideal, very close (walkable) to many shops and restaurants. It's situated on the second floor of a building on a pier, which was very private, quiet, and relaxing. The space was more than large enough for myself and my husband. The kitchen and bathroom were stocked with all needed amenities for a week-long stay. Pam's communication was stellar! She responded quickly when asked about restaurant/bar suggestions to watch our team's baseball game and other non-emergent inquiries. It was obvious she cared about her place and her guests. Her added touches (personal note and chocolates) made us feel welcome. If we ever find ourselves back in Boothbay, there is no doubt we will stay at Pam's place!

On The River 2 with Lucy the resident cat
We have stayed at Patricia's property many times and we will come again. Her art gallery downstairs is always interesting and we are in love with her "cat host" Lucy...she just adores people!

Cottrill House on Damariscotta River # 1
We absolutely loved our stay here! The location was perfect, right in town and right by the water. Lissette was very attentive, gave us a coupon for the place we were going to dinner in town, and then we mentioned we were wanting to do a bonfire and she started it for us! We loved sitting on the private dock and enjoying the river views and being able to walk to get breakfast, lunch, or dinner in town. Highly recommend staying here!

Waterfront Condo at the Sheepscot
We had a lovely night at Audray’s place! The location & the views exceed expectations. It was clean, cozy and inviting. Edited to add- not reducing stars for this because we enjoyed the accommodations, but I want other travelers w/ pets to be aware: Audray reached out 24+ hours after we checked out to say her cleaning person reported “an excess of pet hair on furniture and linens than her washing machine could not handle”, and requested we mail her an extra $50 to cover special laundering. We sent $75 on platform instead as we were shocked and sorry to hear this. We found it surprising b/c were in the condo only 14 hours, we immediately covered the furniture w/ pet covers (we brought our own) upon arrival, we covered the beds w/ our own extra top sheets to protect the quilts from pet hair, & we do not let dogs sleep in the beds- we bring pet beds. We have only received compliments on cleanliness & exclusively 5 star reviews from hosts over 7 yrs and 23 stays all w/ multiple pets.

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front
Our stay at The Bee Keepers Cottage was amazing. The property met our needs perfectly and it was super cute and cozy. The host was very responsive and communicative. And for any star gazers out there, the sky on a clear night is mesmerizing.
Waterfront 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!

Cove House
The house on the tidal river was perfect! My wife loved the extra suite as a get away for reading and watching the wildlife on the river. Easy to get to town by taking the walkway bridge too! Kathy was a great host!

Renovated home with amazing waterfront views
Shirin’s home was the most beautiful and relaxing location I’ve ever stayed in. The view, the sounds of the birds, the space- I couldn’t have asked for more on our hopefully annual Maine vacation. Boothbay Harbor has captured our hearts, and I cannot recommend staying here enough. Close enough to drive 6 minutes to Coastal Maine Boatnic Gardens and just a few minutes to downtown- parking has always been relatively easy (and free) on the street downtown. BOOK TODAY!

Cozy Waterfront Home With Breathtaking Views!!!
We had an amazing time. TJ was very responsive and gave his secrets for fishing! He also accommodated a request that was an overlook on my part. I can’t say enough good things about the place itself or how nice TJ was. It was a phenomenal experience all around!

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: Private Hot Tub, Sauna & Free Massages!
Me and my friends had a lovely time at this lake house, the beds were comfy and there was more than enough room for sixteen of us. The place is very well taken care of and you can tell there is a lot of thought and work put into the home. All the amenities were amazing from the chair to the sauna everything worked great and the hot tub was to die for. We loved our stay and would 100% come again.

Belfast City Park Ocean House
We had a fantastic stay at William's property. This place is a gem, and I absolutely loved the time we got to spend there. The moment you walk into the home and see the living room with its tall, angular windows, and the bay right outside, you know you're in for a treat. The home itself is nicely appointed, particularly the kitchen, which has everything you need, including good quality cookware, an induction range, and a Bosch dishwasher. The bedrooms are large and clean. We had no issues that mattered, but for the sake of being thorough: the master bathtub had an "out of order" sign on it, we couldn't figure out how to turn the shower light on upstairs, and we could also never get a few of the main entry lights to turn on despite our best efforts. None of these things really affected our stay very much, but they're worth noting. This is truly a wonderful home. I hope we can come back someday. I was immediately at peace just sitting on the deck and watching the world go by.
Waterfront apartment rentals

Oceanfront, dog-friendly 2BR with harbor view
Very nice place, totally renovated, spacious, cozy, and comfortable. It is located in a very beautiful area. We will be back for sure!

1BR Waterview | Deck | Partial AC
nice place

2 Rangeley Lake unit 2 Condo Dock, Kayaks and more
This is the second time staying at Debi's Rangeley Lake Condo. It is a perfect location to stay if you're skiing at Saddleback or just exploring the area. Debi is very responsive to any questions. The condo is comfortable and the kitchen has everything you need to have dinner at "home". When we're in the area, we would definitely stay here again.

3-BR Elegant Oceanfront Condo w/ Stunning Views
We can't say enough about the fantastic location and condition of Vacasa Maine's condo. It appeared the furnishings and everything is brand new. The decorating is very attractive and the unit was pristine in cleanliness. The best thing about it is the location. We could not have asked for anything better than to overlook the bay, watch the tide, the boat traffic, and the twinkling lights across the bay in the evening. The shops and restaurant's of Boothbay Harbor are within walking distance. We frequented the restaurant downstairs several times and were not disappointed. This was our first trip to Maine and your accommodations made it all we hoped for. We would definitely stay there again!

Harbor View Cottage Unit A 2 bedroom downtown
What a beautiful location and house. There’s nothing better than sitting in the living room or front porch and being able to see the Belfast Bay. The house is very clean and neat. Beds are comfortable, shower is very hot. Don’t miss the sunrise in the mornings. Overall this is one of our favorite places we have stayed in Belfast.

Samoset Resort Oceanfront Condominium
This place is absolutely amazing. It was larger than expected. It looked smaller in the pictures. Everything in the apartment was squeaky clean and we had every single thing we needed, from pots and pans to board games. Great ocean view from the porch, the living room and from one of the bedrooms. I loved seeing the boats pass by. So peaceful! I stayed there with my elderly mom, my teenage daughter and her friend for 4 days. There was so much to do! We enjoyed both the outdoor and the indoor pool. The kids took advantage of the Health Club by playing ping pong, badminton and going to the video game room. They also spent several hours playing chess in a very nice room near the lounge area that had a gorgeous ocean view. We had dinner at the Italian restaurant in the resort and were impressed by the amazing view. Great service. We also enjoyed the long walk to the lighthouse right next to the resort, and loved going to Camden, such a charming little town, 10 minutes away. The hostess, Laurie, was very accommodating, super nice, and communicated with me frequently, making sure I had all the answers I needed. I would definitely go back there! Glad to have made such wonderful memories! We didn't want to leave!

Cozy Lakeside Studio w/ Private Swimming Area
Really loved this property! The unit provided a very cozy stay, and several amenities were provided. Very quite, peaceful stay and a great view of the lake from the porch! Would definitely plan to stay here again in the future!

Ocean Front - Penobscot Bay - New 4 season home
Simply perfect! Everything in the kitchen is new, in working order, extremely well-stocked. The home is clean and comfortable with amazing fine art everywhere. And the view! We couldn't get enough of the beauty, watching the Ospreys fishing, walking the little beach. Lots of hiking close-by. Rockland has great seafood market, bakery, bookstore. The Transportation Museum is excellent.
Quick stats about waterfront rentals in Oakland
Total rentals
40 properties
Nightly prices starting at
$128 SGD before taxes and fees
Total number of reviews
890 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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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