
Cabin vacation rentals in Oakland
Find and book unique cabins on Airbnb
Quick stats about cabin rentals in Oakland

Total vacation rentals
Explore 20 vacation rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at G$25,102 GYD per night before taxes and fees

Verified guest reviews
Over 270 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
10 of Oakland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oakland rentals

4.9 Average rating
Oakland stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated cabin rentals in Oakland
Guests agree: these cabins are highly rated for location, cleanliness, and more.

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Lakefront Home w/ Dock | Porter Lake | Sugarloaf!
Lakefront paradise on Porter Lake with a private dock, swim float, spacious yard, hammock, deck, patio, grill, fast WiFi, smart TVs, and all the comforts of home. Enjoy direct access to Maine’s ATV and snowmobile trail network right from the property, plus excellent fishing, boating, kayaking, swimming, & ice fishing. Just 20 minutes from Farmington and 35 minutes from Sugarloaf Resort and the Bigelow Mountains. Experience Maine lake living at its finest in every season with stunning lake views

Waterfront private beach. 4-seasons Maine escape.
Waterfront cabin on North Pond in Smithfield, Maine with a private sandy beach just steps from the door. This four-season retreat sleeps up to 10 guests with 3 bedrooms and 2.5 bathrooms. Swimming, kayaking and sunsets in summer, fall foliage views, and direct ITS 87 access in winter for snowmobiling! Easy access for ice fishing. Peaceful, private setting close to Waterville & Augusta. Sugarloaf nearby. Ideal for families, couples, and year-round Maine lake getaways. Book now and unwind! Relax!

Sister a-frame in Woods (A)
Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!

Webber Pond Cabin LLC
Unwind watching the eagles soar and listening to the loons call or fishing off the dock at this inviting log cabin by the lake! This newly renovated cabin has high-beamed ceilings with rustic features throughout and all the modern amenities to make your stay as stress-free as possible.The property is beautifully landscaped, private and the western views provide unforgettable sunsets. Spend your next vacation at the Webber Pond Cabin where you will create memories that last a lifetime!

Hobb’s House - Year Round Log Cabin on the Water
Cozy 2 Beds, 1 pullout sofa bed, 2 Bedroom, 2 Bath Log Cabin with water/mountain views on Hobb’s Pond. Relax on the dock, grill, canoe (1)/kayaks (2)/swim during the day and relax with your streaming services on the smart TV at night. 5min drive to the Camden Snow Bowl for ski/snowboard during the winter. Ice skate on the pond. Rent out a boat during your stay. 13 min drive to downtown Camden for great restaurants and a sunset cruise on a sailboat. Close proximity to hiking trails!

Sunset Chalet Lakefront Hot Tub Game Room
Tucked along the peaceful shore of Belgrade Stream, Sunset Chalet is a private, waterfront escape designed for cozy connection and quiet joy. With a hot tub beneath the trees, a warm fire flickering inside, and a playful game room downstairs, it’s the perfect space to unwind and make memories. Whether you’re celebrating a honeymoon, anniversary, or enjoying a relaxed family getaway, Sunset Chalet offers a setting that feels both special and deeply comforting.

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)
Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.

Price's Point - Cabin on the water
Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

Cozy Lakefront Cabin in Freedom, ME
Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Forest Cabin w/ Stunning Wall of Windows
Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

Private tiny cabin on six acres of trees
The tiny cabin is perfect for any individual or couple looking for a quiet private getaway. This newly renovated space is perfect for reading, sunbathing, napping, outdoor cooking, or walking your dog in the wooded area outback. The central location of the cabin is the jumping off point to other activities such as hiking, kayaking, whitewater rafting, bicycling, or exploring Farmington, a hip little college town nearby.
Popular amenities for Oakland cabin rentals
Cabin rentals with a hot tub

Maybelle the Tiny Cabin on 100 acres

Birch Hill Cabin w/Hot Tub

Log cabin, stunning views, hot tub, fire pit

Cozy Cabin with Modern Amenities. Pet Friendly!

Apres Ski Haus - Private Oasis

Raven's Crossing - Kate's Cottage

Romantic Hidden Cottage!

Modern Cabin on Crie Hill
Pet-friendly cabin rentals

Loon Lodge

‘Round the Bend Farm - private, modern cabin

Trailside Cabin

Smitten - you will be - Hear Silence.

Mill Pond Waterfront Cabin On The Way To Sugarloaf

Modern Tiny Cabin Near Belgrade Lakes

Escape at Great Pond

Lake Front Cabin of Belgrade
Private cabin rentals

Cabin In The Birches #2

Lake Cabin in the Trees

Misty Mtn. Lodge

Birch Cottage · Just You & Quantabacook Lake

Quiet LAKE Retreat >Relax-Unwind-Connect-Nature

Grace Landing

Bear Cub Lodge

Quaint Getaway Round Pond - Kayak, Bonfire, Fish
Destinations to explore
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- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Saddleback Ski Mountain Maine
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Camden Hills State Park
- Farnsworth Art Museum
- Maine Lighthouse Museum
- Cellardoor Winery
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Black Mountain of Maine
- Belgrade Lakes Golf Club
- Range Ponds State Park
- Lost Valley Ski Area
- Sugarloaf Golf Club





