
Holiday houses in Oakland
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Top-rated holiday rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Oakland

Farm stay in Oakland
5 out of 5 average rating, 3 reviewsCharming Country Farmhouse on Farm - Pets welcome!
LisaRating, 5 stars1 month ago
True to the description, I found Kathleen's 1840's farmhouse to be charming. You could really feel the atmosphere of the place with wide plank flooring, tall windows, and a peaceful, homey feel. The house was also modern in the ways that count - like a sumptuous tub, well-appointed kitchen, comfortable bed and spotless bathrooms. I appreciated several thoughtful touches and really enjoyed an evening walk across the pasture and into the woods. Kathleen was a great host and very responsive to my questions. I'll be returning soon.
Guest favourite

Home in Waterville
4.9 out of 5 average rating, 136 reviewsSterling House
DeirdreRating, 5 stars3 weeks ago
Great location for activities at Colby College. The house had everything we needed.

Guesthouse in Oakland
4.57 out of 5 average rating, 14 reviewsSunny Studio in Belgrade Lakes Region
HollyRating, 5 stars44 months ago
My husband and I had a wonderful one night stay at Abbie’s place. Check-in was a breeze as well as finding the location and parking. The space is private and spacious and equipped with anything you may need for an extended stay (fridge, stove, microwave, dishes, etc.), and the bed is very comfortable, which was a bonus after traveling and hiking for multiple days. My husband and I woke up so refreshed after our stay, and I would recommend anyone to book Abbie’s place.

Cabin in Belgrade
4.58 out of 5 average rating, 184 reviewsMoon Country - Rustic Camp Sustainable Getaway
ChloeRating, 5 stars8 months ago
My husband and I had the most relaxing stay ! The home and land was beautiful. Very rural. I would consider it a glamping experience, which was exactly what we were looking for. We brought battery powered string lights to hang around the place which made it easy to see at night . The train ran once early evening and once in the morning , but was never an issue . It was fairly easy to bring a bucket of water to from the lake for the toilets. We will definitely come back!
Guest favourite

Guest suite in Oakland
4.96 out of 5 average rating, 23 reviewsWelcome to Squirrel Pocket!
ToniRating, 5 stars1 month ago
Betsy was a lovely host, was very gracious and explained about the current construction next door and the train nearby. The view was beautiful, even in the rain. Was very peaceful. Thank you Betsy!
Guest favourite

Cabin in Hope
5 out of 5 average rating, 15 reviewsCozy Lakefront Cabin - Hope Floats
WillRating, 5 stars3 weeks ago
Spent a relaxing long weekend at the cabin. Idyllic location right on the water with plenty to do outside. We enjoyed making fires, fishing, and exploring in the canoe. Inside, the cabin was thoughtfully decorated and very comfortable. Camden is nearby for a nice dinner or a stroll and shopping downtown. Acadia is also close enough for a day trip. Checkin/checkout was very straightforward, and the host was helpful and quick to answer any questions. Hope to visit again!

Cabin in Fairfield
5 out of 5 average rating, 7 reviewsCabin In The Birches #2
LizRating, 5 stars8 months ago
The cabin was perfect for our stay. We made dinner and Misty was quick to deliver a baking sheet and olive oil when we asked if she had them. She was great to talk to and shared info about DoorDash and other amenities. Would def stay again.

Cabin in Oakland
5 out of 5 average rating, 4 reviewsYour Path to Tranquility
SarahRating, 5 stars10 months ago
This place was even better than the photos show! We had such a fantastic week! Every inch was spotlessly clean and they have provided everything you could possible need. All you need to bring is clothes, food and a beech towel. The furniture is very comfortable, including the beds! The screen porch, the dock and in the water were our favorite places to hang out. The swimming was fabulous, we recommend bringing water shoes as it's a little bit rocky but it wouldn't be a problem if you didn't have them. The kayaks and paddle board were great fun and a fire in the fire pit was a great way to end the day. Peter was very quick to answer any questions and super accommodating - He made sure we had plenty of firewood for the fire pit and propane for the grill. It is such a relaxing and fun place to be, we hope to go back next year!
Quick stats about holiday rentals in Oakland
Total rentals
70 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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