House holiday rentals in Oakland

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Oakland

House rentals with a pool

Superhost
Home in Turner
4.84 out of 5 average rating, 70 reviews

The Getaway- River Paradise

DavidRating, 5 stars4 months ago
every thing was great. I had to get in touch with David when we first arrived and he got back to me immediately. Everybody like it. We will certainly get in touch with David when we come back to Maine. The only thing I would do If I were David is put the house numbers on the mailbox, we were concerned we were going to the right house but really no problem
Guest favourite
Home in Liberty
4.89 out of 5 average rating, 62 reviews

Luxe Liberty: Getaway with Heated Indoor Pool!

AlisonRating, 5 stars4 days ago
The house is beautiful and as described. We had 2 adults and 4 teen/pre-teens and it was amazing. So much space to spread out. It was very windy during our stay, but we stayed warm in the pool and hot tub. We were not used to so many stairs, but for sure got a workout in! The beds were all very comfortable. We would for sure book again and have had multiple friends already book after seeing our pitcures. The hosts were very responsive and friendly and made our first airbnb stay memorable.
Superhost
Home in Carrabassett Valley
4.71 out of 5 average rating, 24 reviews

*New to Market* 410 Snowflower

KristinaRating, 5 starstoday
Chris was super responsive to every question and a great host. The place was clean and cozy! Had everything we needed for our little ski getaway with friends! He was even able to get us a new coffee pot and cookware set before we checked in! The place is very convenient for ski in/ski out. Just a little over 200 yards to the Snowbrook Trail to ski down to snubber lift! Unfortunately the hot tubs (there are 2 in gazebos as you walk to the trail) were closed during our stay (looks like they’re only open Friday through Sunday) but would be a great addition if you’re there during the weekend! Excellent place! Excellent host! You don’t want to miss this one!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars5 months ago
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Top guest favourite
Home in Standish
4.94 out of 5 average rating, 50 reviews

6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK

ZachRating, 5 stars7 months ago
Perfect place for a group or big family! Was much larger than expected, very private, and had so many cute touches and details that made our stay unforgettable. I could not recommend this place enough!
Guest favourite
Home in Rockport
4.96 out of 5 average rating, 52 reviews

Dog Friendly Midcoast Cape

SarahRating, 5 stars5 months ago
BEAUTIFUL Home!! Tons of space to relax and spread out with our family! The beds were very comfortable! We really appreciated all of the bathrooms for our group! The kitchen was huge and so handy for preparing meals! I absolutely loved the style and atmosphere of this wonderful home! We also loved being able to bring our dogs!! We had a lovely time and we would most definitely come back!!! 🥰
Superhost
Home in Windham
4.73 out of 5 average rating, 11 reviews

Gorgeous Maine House Close to Sebago Lake

AmyRating, 5 stars7 months ago
This was our second stay at Craig's place. It is a perfect home for our two families which include a 2, 4, and 14 year olds. there is plenty of space and the pool area and indoor basketball gym are such an amazing treat! We were happily surprised to find a new mini split in the large game room which cooled the whole downstairs.
Superhost
Home in Raymond
4.8 out of 5 average rating, 10 reviews

Turtle Cove Sebago Lake Private Waterfront & Pool

VirgenRating, 5 stars3 months ago
Beautiful property! Great Lake view! We had a wonderful time!

Weekly house rentals

Guest favourite
Home in Rangeley
4.81 out of 5 average rating, 58 reviews

Snowmobile SKi ATV in Rangeley 3 bedroom home

NathanRating, 5 stars2 weeks ago
This was our second time staying at this house and it was great again. The seating area off the main living room and kitchen was open this year and added a lot to our stay. Had a great week. Definitely recommend!
Top guest favourite
Home in Newcastle
4.96 out of 5 average rating, 45 reviews

Cozy & quiet on the river... the Captain's House

UtpalRating, 5 stars7 months ago
The hosts were very prompt in communicating. The thoughtfulness they have put into furnishing the property is amazing. It has a very vintage nautical feeling to it. The house is extremely well appointed. We didn’t have any problems at all. The surroundings are off the beaten path which we especially appreciated. It’s a short 10 minute drive to Damariscotta Downtown. I would highly recommend this property.
Superhost
Home in Rangeley
5 out of 5 average rating, 3 reviews

Russell Cove 18 | Shared Access to Rangeley Lake

KathyRating, 5 stars2 months ago
The whole process was easy and communication was great. The house was perfect for our family of 8. We’ll definitely be back. Thank you!!
Guest favourite
Home in Ocean Point
4.93 out of 5 average rating, 45 reviews

137 Shore Road Ocean Point view now with WiFi

ThomasRating, 5 stars5 months ago
Jerry's house was a great location with terrific views. The house was tastefully decorated and immaculate. A perfect Maine getaway that we cannot wait to go back to in the future.
Guest favourite
Home in Brunswick
4.98 out of 5 average rating, 50 reviews

Oceanfront, Mere Point year round home Brunswick

E ThomasRating, 5 stars5 months ago
Loved the layout of the house. Great kitchen and master bedroom. Master bath a little cramped. Enjoyed the view and outdoor seating.
Guest favourite
Home in Naples
4.73 out of 5 average rating, 15 reviews

Pinecrest Lakefront, Private 1 Bedroom

DavidRating, 5 stars1 month ago
Found this home because we needed a place with EV charging, but super glad we landed here! Wonderful home in a wonderful location (and it has 2 EVSEs!). I like the 1 bedroom strategy…that makes a ton of sense for providing access to a home when full utilization is not needed. The superbowl on a 85 inch TV with a Sonos arc system was fantastic!
Guest favourite
Home in Camden
4.93 out of 5 average rating, 131 reviews

Cozy Cottage With River View

NatalieRating, 5 stars3 days ago
Jeremy and Ellen are fantastic hosts. Very communicative during booking and prior to arrival with suggestions of what to do (we were travelling from the UK). We stayed for 16 nights and the house felt like home - it has everything you need. Absolutely fantastic place to stay and we really recommend it.
Superhost
Home in Rockland
4.64 out of 5 average rating, 50 reviews

Downtown "NamaStay"

SunitaRating, 5 stars6 months ago
Annie's place is a clean, well kept older home. We really appreciated her accommodating our early check in, so we could be on time for our tour. The home is well stocked with linens and towels and in a great location. We were able to walk to downtown with delicious restaurants and shops. Our family was happy to each have a bedroom to sleep comfortably, and having air conditioning as an amenity was very helpful in our decision to stay here. Thank you Annie for your suggestions and hospitality for our stay in Rockland :)

Private house rentals

Guest favourite
Home in Northport
4.93 out of 5 average rating, 28 reviews

Close to the Beach, Hiking, Golf course, and Town!

ValerieRating, 5 stars2 months ago
Our family and I had a wonderful stay at Jackies, we are all originally from maine, and her home gives you everything great about maine. We really felt at home, it snowed christmas eve which made it even more beautiful ( The driveway was plowed out early as well). I brought a small christmas tree with us on our trip up, and when we walked in, the place was decorated for christmas, which was just amazing and so thoughtful. We definitly plan on staying again, the next time we are back in maine. Thank you again Jackie!
Guest favourite
Home in Belfast
4.96 out of 5 average rating, 138 reviews

Cove House

SusanRating, 5 stars4 months ago
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.
Guest favourite
Home in Liberty
4.98 out of 5 average rating, 87 reviews

Kirby Island Road Retreat

BlakeRating, 5 stars3 weeks ago
Loved staying at this cabin! I was a last minute booking and the hosts were super nice and accommodating. Would recommend these hosts and this cabin to everyone!!
Superhost
Home in Harpswell
5 out of 5 average rating, 36 reviews

Oceanfront Luxury Estate in Mid-Coast Maine

SharonRating, 5 stars5 months ago
This was such a wonderful property for my family -- beautiful and peaceful with lovely views. We loved spending our days out in the spacious yard, playing lawn games, sitting around the fire pit, and fishing, and eating all our meals out on the patio. Everyone left feeling very relaxed and happy. Thank you Pam and David for sharing your home!
Guest favourite
Home in Bremen
5 out of 5 average rating, 10 reviews

Authentic Maine Harbor 5 Bedroom Home

RandallRating, 5 stars5 months ago
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.
Guest favourite
Home in Belfast
5 out of 5 average rating, 14 reviews

4bed Full House on Private Dr. w/ Large Yard

AndrewRating, 5 stars1 week ago
Destioney was amazing to deal with. The house was beautiful and we felt right at home the entire stay. The welcoming basket was a favourite!!!! Highly recommend this stay!!!
Guest favourite
Home in Naples
4.99 out of 5 average rating, 108 reviews

LUX Designer Private Waterfront

AdinaRating, 5 stars3 weeks ago
Beautiful and secluded place, was very clean and communication was great. Would definitely come again
Guest favourite
Home in Yarmouth
4.92 out of 5 average rating, 525 reviews

Beautiful Coastal Maine Getaway

DaniRating, 5 stars3 weeks ago
Thank you for your hospitality and your responsiveness to our needs during our stay. We really enjoyed visiting your home and hope to do so again in the future.

Quick stats about house rentals in Oakland

  • Total rentals

    20 properties

  • Nightly prices starting at

    £39 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Oakland
  6. House rentals