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Vacation rentals in Oakland

Vacation rentals in Oakland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Lake-House  on water, East Lake, Belgrade Lakes
SUPERHOSTEntire cottage · 7 guests · 11 beds · 1 bath
Lake-House on water, East Lake, Belgrade Lakes

Welcome to the Lake House! 5 bedrooms. Access to a mooring. Newly 2018 renovated full bathroom and kitchen. Bedrooms have locked doors & WiFi. This cottage has a Deck and Docks, new BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances. Row & Paddle boat, 2 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Float use with neighbors permission only. Near Public Boat Landing & country store. I reside nearby, I will help with any issues.

What guests are saying:

“Mark's house is great, I felt like I was in heaven, clean, with everything we needed and more, he was always attentive if we needed something, we went to the museum in Augusta and Snow Pond Cruises, this vacation was an unforgettable experience. Thanks Mark to the opportunity to had the best birthday ever.”

Kate-Ah-Den Cabin,  a soul soothing escape.
SUPERHOSTEntire cabin · 3 guests · 1 bed · 1 bath
Kate-Ah-Den Cabin, a soul soothing escape.

Secluded & artistically built - a new cabin on top of Hampshire Hill. Relax and enjoy the views, take time to hear yourself think, or go explore 75 acres of private woods w 2 miles of private trails. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec trails, snowmobile trails, Farmington & Augusta. 1 hr south of ski resorts. Great for stopping for 1 night or for taking a week to escape from the world.

What guests are saying:

“Kate’s cabin was the perfect discovery for us! We were looking for a place to escape every day quarantine life in the MA suburbs and relax with zero obligations. Well, wow, we found that at Kate-Ah-Den! The other reviews are right- the photos are great and obviously convinced us to choose this listing, but they don’t do this beautiful cabin justice. We drove up and were immediately in awe of the view. The cabin is pristine and every detail is so thoughtful, the finishes have such character, there are plenty of places to hang out and enjoy the view. The screened-in porch, was our fave with the screened-in gazebo as a close second. It’s nestled into the trees and feels so cozy withOUT the bugs! Perfection! The nature sounds are so wonderful, the view truly is incredible no matter the weather, and the energy of this wonderful place is really great. I was able to use the WiFi to lead a few Zoom classes, so that was a win too! The guestbook is full of little notes from previous guests and it’s clear that this place is attracting high-vibe people. Knowing that didn’t surprise me, but felt really good. Kate is a wonderful host and was in communication prior to and during our stay as needed. She is so kind, generous, and welcoming. I’ve already sent the link to friends who have asked and highly recommend Kate-Ah-Den!”

Anchor House. Private Suite near Colby and Thomas
SUPERHOSTPrivate room · 4 guests · 1 bed · 1 private bath
Anchor House. Private Suite near Colby and Thomas

Anchor House welcomes you! We offer a private entrance into an apartment style space. There is a spacious bedroom with a queen bed and a private bathroom. This space also has its own living room with flatscreen TV, sofa bed, roll away cot. We are minutes from Colby and Thomas Colleges, the Waterville opera house and I 95. 3 nearby launches for kayaks & canoes. We offer coffee, tea, hot chocolate, instant oatmeal. Microwave, toaster, and a refrigerator. Driveway parking. Pet Friendly. WiFi.

What guests are saying:

“Great historical place to stay in Waterville, Maine. Dana's house has so many lovely little touches- I may have indulged more than I should have in the chocolates dish- sorry Dana! Good communication leading up to our arrival, and we felt very welcome when greeted at the front door.”

Holiday rentals for every style

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Popular amenities for Oakland holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Oakland

A little piece of heaven
SUPERHOSTEntire apartment
A little piece of heaven
Price:$183 NZD / night
Loon Haven
Entire cottage
Loon Haven
Price:$251 NZD / night
In town bright and sunny cape retreat in Augusta!
SUPERHOSTPrivate room
In town bright and sunny cape retreat in Augusta!
Price:$60 NZD / night
Haven Hill Cabin #2
SUPERHOSTEntire cabin
Haven Hill Cabin #2
Price:$115 NZD / night
Wellness Gardens Retreat
SUPERHOSTPrivate room
Wellness Gardens Retreat
Price:$58 NZD / night
Rustic yet perfect with some luxuries.
SUPERHOSTEntire guesthouse
Rustic yet perfect with some luxuries.
Price:$168 NZD / night
Griffin's Rest; Inviting, Cozy, Near Thomas/Colby
SUPERHOSTPrivate room
Griffin's Rest; Inviting, Cozy, Near Thomas/Colby
Price:$58 NZD / night
Room D - free bikes,  kayaks, hot tub & sauna
SUPERHOSTPrivate room
Room D - free bikes, kayaks, hot tub & sauna
Price:$54 NZD / night
Spectacularly clean private apt, hosts live above
SUPERHOSTEntire apartment
Spectacularly clean private apt, hosts live above
Price:$113 NZD / night
Bev's Lake house.
Entire house
Bev's Lake house.
Price:$206 NZD / night
Oakland
SUPERHOSTPrivate room
Oakland
Price:$84 NZD / night
2 bedroom home Colby College <2 miles Waterville
SUPERHOSTEntire apartment
2 bedroom home Colby College <2 miles Waterville
Price:$202 NZD / night
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