
Waterfront vacation rentals in Oakland
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Top-rated waterfront accommodations in Oakland
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Popular amenities for Oakland waterfront rentals
Waterfront apartment rentals

Large Home with Great View next to horse farm
Great house and good location, it was warm during our stay. Enough space for our company. Not far away from the city. Overall it was nice staying there.

Stunning Royal Richmond 2 Br Apartment Get Away!
This apartment was spacious, quiet and comfortable. Perfect for two couples.

On The River 2 with Lucy the resident cat
Great little spot right in town. Super convenient for walking to shops and restaurants. The apartment was clean, comfortable, and had a lovely view of the river, which made for a relaxing morning. Bonus: the very sweet cat, Lucy, who made the stay even cozier. Would definitely stay here again!

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.

Welcome to "West Winds at Pemaquid"
We had a great stay here. The apartment was perfectly clean and well appointed. Bob and Laura covered everything; thoughtful snacks, a comprehensive guest book, fully stocked kitchen and they even made umbrellas available. We were super comfortable and it was a great spot to base our Bristol adventures from!

Falmouth Waterfront Carriage House Apt
I have stayed at Anne’s place many times. Anne and her husband are always very nice and friendly. The apartment is spotless, comfortable and you can’t beat the location, just up the hill from charming Falmouth Town Landing and beach and an easy drive to downtown Portland.

"Ship Shape": waterfront, cozy studio- downtown
Excellent spot and fast response from Grace for a last minute reservation. Clean, and everything needed. Shower was hot, heat great on a cold night after a long day's work.
Waterfront house rentals

Lakehouse with 100ft of private waterfront
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!

Open concept 4 bedroom Lakehouse
Great winter weekend stay in Maine, the house was very cozy and perfect for our group. The location is perfect for access to the ski mountains and the town as well. Overall highly recommend Roman’s place, I’m sure it is just as beautiful in the summer!

Authentic Maine Harbor 5 Bedroom Home
The house was exactly what we were looking for: relaxing with great views. The marina with fresh seafood within walking distance was icing on the cake.

5Bed- Hot Tub - Sauna-Pool Table -Lake Front, Pets
We had a great, low key girls weekend at Alanna’s place. The hot tub was great for soaking in, and right off the deck. We brought our snowshoes and enjoyed snowshoeing down to the lake and around the property. The tvs in the living room felt a bit over powering, but we figured out how to put two to sleep so we could just listen to music on the third.

Spring River Retreat with Hiking Trails
Wonderful relaxing getaway! We loved hiking the trails from the property and relaxing on the deck overlooking the river. Pip was an excellent host, and we would love to come back another time!

New Listing! Waterfront Round Pond Home
What an amazing spot! My family and I enjoyed mornings on the dock, watching spectacular sunrises and daily sightings of bald eagles. The walk down to the dock was lined nicely with stone steps and once on the dock it was hard to leave. The three kayaks allowed us to explore the coastline and although the shoreline was rocky, we enjoyed a dip in the cool September waters. The house was perfectly decorated and equipped with everything and anything needed. Lisa was great to work with, quick to answer any questions and accommodating with requests. The beds were extremely comfortable and the view of the sunrise each morning, priceless. The location was perfect, within minutes from a venue where we were attending a wedding and a few restaurants, although we hated to leave the house. I would highly recommend staying at this beautiful home that slept seven of us comfortably. If you're looking for a peaceful spot with stunning views, this place is perfect. We would love to visit again.

2 BR Waterfront house with stunning view.
This was a really nice house on a beautiful lake. The beds were comfortable and there were enough to accommodate us. It was very clean and easy to enjoy your stay. We really enjoyed our stay.

Tree House - Mooselookmeguntic Lake
My family and I throughly enjoyed staying at the tree house. It’s right on the water to offer that camp feel yet also has a blend of that modern, small and cozy feel. Staying there was great, the house had all the basics one could need which helped make our stay that much easier. Unfortunately the weather was overcast most of our stay so we didn’t have a chance to fully enjoy the lake front view and dock, but our one moment where it was warm enough to jump in the water didn’t disappoint. Wish we had more opportunity to spend time down by the water. We’ve been to the Rangeley area before but this was our first time staying on this lake, we were also able to hike bald mountain and drive up quill hill in rangeley. There is plenty of spectacular views in the area and plenty of things to do. Next time we think of staying in the area we will certainly have this place in mind. We definitely would recommend staying here!
Waterfront condo 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!

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.

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.

1 Rangeley Lake Unit #1 In town condo with dock
Well stocked with all the amenities. Just missing a can opener! Upstairs was very hot, but Debi said they are putting in a/c for next year. Beds were very comfortable. Awesome location, watched a family of deer and a family of ducks all week. Great access to the lake! Debi is very friendly and helpful. We'll definately be back!

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!

Waterfront Condo: Walk to Downtown Boothbay Harbor
We have been staying at various places around North America and can say — without question — this was the nicest/all-around properties we have ever stayed at during our lengthy relationship. As I told the property owner, who by the way is a fabulous person, the photos of the Signal Point home don’t do it justice. The home is even more beautiful in person. We have also never been in a house as perfectly stocked with amenities in our lives. There was a ton of paper products already there for us. The linens were in abundance galore. And the gift bag for us when we arrived was an awesome touch that you don’t get everywhere. Bottom line, we have been staying in Boothbay Harbor for close to a decade during our Maine visits. And this is the best property we’ve been fortunate to land for our trip. We will be back next year and years to come before we buy our own place at Signal Point!
Quick stats about waterfront rentals in Oakland
Total rentals
40 properties
Nightly prices starting at
$138 CAD 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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- Saddleback Ski Mountain Maine
- Fox Ridge Golf Club
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Pemaquid Beach
- Samoset Resort
- Dragonfly Farm & Winery
- Pinnacle Park
- Maine Maritime Museum
- Spragues Beach
- Coastal Maine Botanical Gardens
- Sugarloaf Golf Club
- Narrow Place Beach
- Hermon Mountain Ski Area
- Bear Island Beach
- Martindale Country Club
- Lost Valley Ski Area
- Black Mountain of Maine
- Rockland Breakwater Light
- Farnsworth Art Museum
- The Camden Snow Bowl
- Titcomb Mountain
- Eaton Mountain Ski Resort
- Islesboro Town Beach