
Holiday rentals with a kayak in Oakland
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Oakland

Total holiday rentals
Explore 40 holiday rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at $155 NZD per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 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!
Top-rated Accommodation with a Kayak in Oakland
Guests agree: these holiday homes with a kayak 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 with 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

Forest Bathing Lake Tiny Home: Kayak Fish Fire Pit
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

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!

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Stella the Studio Apartment
Stella is a cabin-style, pet-friendly studio apartment on 100 acres of wooded property. Enjoy the property's amenities (trails, kayaking, canoeing, axe throwing, wood-fired pizza oven) and return to your comfortable space with a hot tub, power, heat, and plumbing! Stella is located at the start of the land, above our storage building, has plenty of parking and can be reached with 2wd vehicles. This is a new space, exterior is unfinished. The hot tub is an Aqualiving 3 person lounge!

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Lake-House on water, East Lake, Near Waterville
Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.

Visit Beautiful Home on Snow Pond
Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.

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.

SkyView Treehouse | Lakefront • Private Hot Tub
Welcome to your dream treehouse escape — tucked among the pines with stunning lake views, a private hot tub, and direct access to Belgrade Stream. Designed for couples, honeymooners, and small families, SkyView Treehouse offers a luxurious retreat in nature. Enjoy starry nights in the hot tub, cozy evenings by the fireplace, and peaceful mornings on your private deck. Rustic charm meets upscale comfort in this unforgettable lakeside getaway.

Beautiful Maine Lakeside Cottage
This beautiful cabin on the Lake is perfect for fun and relaxation, including swimming, kayaking, fishing, and more. Enjoy your morning coffee on the enclosed porch overseeing all of the beauty that Maine has to offer, with beautiful lakeside sunsets in the evening. Two complimentary kayaks and life vests are provided. The Vista winery is just 2 miles away and offers amazing views and drink selections.
Popular amenities for Oakland kayak rentals
Holiday House Rentals with a Kayak

Mirror Pond Cottage

Kirby Island Road Retreat

Cozy Waterfront Home With Breathtaking Views!!!

Lakefront: Private Hot Tub, Sauna & Free Massages!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Modern Lakefront Home w/ Hot Tub • Summer Vacation

Lakefront 3 bedroom pet friendly on Messalonski

Farm house, River, Island, animals & private Chef.
Cottages with a kayak

Waterfront cottage with spectacular sunset views!

Lake House on Three Mile Pond with Amazing views

Waterfront Lake House, Kayaks, Fire Pit & Fishing

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Coastal Waterfront Cottage in West Bath

Hidden Haven A Rustic Retreat In St. George, Maine

Duck Lane Cottage | Lakefront w/ Dock & Kayaks

Cozy waterfront home on Merrymeeting Bay.
Cabin rentals with a kayak

Hobb’s House - Year Round Log Cabin on the Water

Waterfront private beach. 4-seasons Maine escape.

Peaceful & private waterfront cabin

Cabin In The Birches #2

Elegant Cabin on Great Pond

Cozy Lakefront Retreat

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Birch Cottage · Just You & Quantabacook Lake
Destinations to explore
- Montreal Holiday rentals
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- Quebec City Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Bar Harbor Holiday rentals
- Salem Holiday rentals
- New Haven Holiday rentals
- Rentals with a washing machine and dryer Oakland
- Pet-friendly rentals Oakland
- House rentals Oakland
- Rentals with outdoor seating Oakland
- Waterfront rentals Oakland
- Cabin rentals Oakland
- Family-friendly rentals Oakland
- Rentals with a fireplace Oakland
- Rentals with lake access Oakland
- Rentals with a patio Oakland
- Rentals with a fire pit Oakland
- Rentals with a kayak Kennebec County
- Rentals with a kayak Maine
- Rentals with a kayak United States
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Saddleback Ski Mountain Maine
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Black Mountain of Maine
- Belgrade Lakes Golf Club
- Lost Valley Ski Area
- Sugarloaf Golf Club
- Range Ponds State Park





