
Waterfront holiday rentals in Oakland
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Top-rated waterfront accommodation in Oakland
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Popular amenities for Oakland waterfront rentals
Waterfront apartment accommodation

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!
The apartment is beautifully designed, spacious, relaxing, and comfortable. What more could you ask for? We enjoyed our 3-night stay. Read some of the assembled books on birds and enjoyed delicious food at the local restaurants. Alice was a gracious and responsive host. You will truly love staying in her apartment!

Sail Loft - Upscale Oceanfront on a Pier near BBH!
In short, a unique experience where we met a few extremely friendly people. The property has amazing views of the harbor without noisy working boats. We would out this at the top of our rental experiences.

On The River 2 with Lucy the resident cat
we always look forward to having a good stay here when its 1 day or a couple. Patricia is always friendly and always helpful for the area. Great host and great spot. highly recommend

Cottrill House on Damariscotta River # 1
Very comfortable. Terrific location. Lissette was very attentive, friendly and helpful. Would recommend her home to family and friends.

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.

Caratunk Waterfront Studio
This is a great spot, convenient to lots of outdoor activities in the area. The studio has super comfortable beds, a very well equipped kitchen, and even some nice touches like throw blankets, books, and games for days you want to stay in and get cozy.
Waterfront house rentals

Sugarmaple Lakehouse - Sebasticook Lake Newport ME
Great location. Woke up to the sounds of birds. very responsive. I would have given it a 5 star all the way, David was amazing and responded in a very timely manner. But, the turn over service could have been much better. The previous guest left a wine bottle in the automatic fridge ice dispenser and it was unfounded until my family found a large peice of glass in their drink, serious hazard to drink glass. Should have been spotted by the turn over service but, who would check the ice maker for a bottle a wine? I understand that. Very uncommon and unfortunate for us. David responded in a very fast manner and gave us options to accommodate the situation. I would have left a 5 star if this was the only thing but everything was so unorganized in the kitchen, they had everything but nothing made sense to why it was there. Sink didn't drain. There were also stains on the sheets and a pizza box left by the fridge that wasn't ours. Little things but the turn over service was a let down.

Cove House
We have been going to this area of Maine for over fifty years. I found this gem several years ago and haven’t stayed anywhere since. I find it to be peaceful, walkable to the center via footbridge, it’s all that we want. Kathy is a great host, quickly responds to any questions or needs you may have. We always know we will have a great experience staying here.

LUX Designer Private Waterfront
We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

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!!

Waterfront Farmhouse with Modern Flair!
We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
My wife and I completely enjoyed our stay at Ani’s place. She literally thought of everything any guest could ever want. Beautiful surroundings…walking distance to the Fish Ladder….a couple of miles to all the restaurants downtown. And the place itself is immaculate. The kitchen was perfect for eating in every night. This place is an absolute no-brainer to rent and we can’t wait to return!!!
Waterfront condo accommodation

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
$166 NZD 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
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Rockland Breakwater Light
- Three Island Beach
- Spragues Beach
- Pinnacle Park
- Eaton Mountain Ski Resort
- Narrow Place Beach
- Lost Valley Ski Area
- The Camden Snow Bowl
- Bear Island Beach
- Pebble Beach
- Black Mountain of Maine
- Martindale Country Club
- Farnsworth Art Museum