
Cabin holiday rentals in Oakland
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Top-rated cabin rentals in Oakland
Guests agree: These cabins are highly rated for location, cleanliness and more.

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. Please note some amenities are seasonal. Check out our other listing!

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 from the deck, 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!

Off-Grid Escape. 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- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Smitten - you will be - Hear Silence.
SMITTEN at The Appleton Retreat is a contemporary near off grid cabin that offers all of the comforts of home in total privacy, including excellent WIFI. The Appleton Retreat encompasses 120 acres hosting seven unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1,300 acre preserve and Newbert pond. If you need a time out and desire to embrace nature's way, Smitten is the perfect place to experience a memorable getaway.

Hand built cabin overlooking a pond
Beautiful hand built cabin, overlooking Cotton Pond. Ten minutes from Camden, the sailing mecca of the east coast. Solar lights, (we are off the grid) gravity fed kitchen water, gas-hot water outdoor shower, outhouse overlooking the forest. Hiking trails everywhere! Swimming across the road on Hobbs Pond. If you book in November, there is a possibility that if it gets cold, you will not have a hot outdoor shower and will use water from a 5 gallon ceramic container for drinking and cooking.

Roxie the Tiny Cabin on 100 acres
If all you need is a bed and a bathroom & hot tub, Roxie is the cabin for you! A comfortable full-size bed, composting toilet, a mini fridge & woodstove and electric heater are here for you in this cozy 8x12 cabin in the woods. 2wd access & a parking spot near your door. Hike trails, kayak, fishing, cross-country skiing, or snowshoeing then return to your little space to relax & enjoy! A firepit with wood, an outside table and hammock chairs. 24/7 Guest restroom with shower

Cozy Cabin with Modern Amenities. Pet Friendly!
Kick back and relax in this beautifully renovated home with amenities you didn't know you were missing. Despite its small stature, every square inch is utilized, boasting 4 beds and 1.5 bathrooms, including a huge shower with multiple shower heads and hurricane force water pressure. Located on a quiet street just minutes from the Kingfield village, steps from the snowmobile trail system, and 20 minutes from Sugarloaf. Designed with dogs in mind, complete with a fenced in backyard.

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Mill Pond Waterfront Cabin On The Way To Sugarloaf
***Please Message me to ask about possible discounts and length of stay minimums.*** Year round waterfront Cabin Located on a private road off Rte. 27 & on the way to Sugarloaf. Only 15 minutes to Farmington, about 30 to Carrabassett Valley & Sugarloaf area and about an hr. to the Rangeley and Saddleback Mtn. area. The cabin is situated on 2+ acres with tall trees and plenty of wildlife. Come relax on the covered porch overlooking the pond or around the fire pit

Birch Hill Cabin w/Hot Tub
Birch Hill Cabin is set on the side of a hill, surrounded by almost 8 acres of woods. The cabin is 288 square feet, and the bathroom is detached and located approximately 20 feet from the cabin. A hot tub is conveniently located off the deck for ultimate relaxation! This cabin is tucked away, surrounded by nature! But also conveniently located to so many wonderful spots in the Midcoast! Come enjoy the peace and quiet, where you can rest and recharge!

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.
Popular amenities for Oakland cabin rentals
Cabin rentals with a hot tub

Lake View Hide Away

Raven's Crossing - Kate's Cottage

Apres Ski Haus

Cozy Lakefront Cabin * CampChamp

Lakefront Log Cabin privacy-boats-fishing-hot tub

A-Frame Getaway | Hot Tub | Pool Table

Romantic Hidden Cottage!

Modern Forest Cabin w/ Private Hot Tub & Fire Pit
Pet-friendly cabin rentals

Quaint & cozy cabin in beautiful wooded setting

McKeen's Riverside Retreat

Desert Pond Log Cabin

Cozy Cabin on the Carrabassett River

Trailside Cabin

3 Evergreen

The Birch Bark Cabin

Webber Pond Cabin LLC
Private cabin rentals

Lake Cabin in the Trees

Quaint Getaway Round Pond - Kayak, Bonfire, Fish

Romantic Pond Cabin | 65 Private Acres + Kayak

EcoCabin, for 2-4, 90 mi view

Chickadee A-Frame

Charming 2 bedroom cabin on Clearwater lake

Cabin In The Birches #2

Birch Cottage · Just You & Quantabacook Lake
Quick stats about cabin rentals in Oakland

Total holiday rentals
Explore 20 holiday rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at $126 AUD per night before taxes and fees

Verified guest reviews
Over 250 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
10 of Oakland holiday 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!
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