
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 $116 SGD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Oakland holiday rentals include wifi 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 rentals with kayak in Oakland
Guests agree: these rentals with 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)

Maybelle the Tiny Cabin on 100 acres
Maybelle is an 8x18 cabin with a full-size loft bed, a Cubic Mini Woodstove (wood provided), Natures Head Composting Toilet and Jetsetter massaging hot tub. Kayaks, paddle board, & canoe included . Hiking trails (some solar lit) surround your cabin. Outside is a fire pit and a quick path to the water. Maybelle's kitchen has all the cooking essentials and there's a small propane grill outside & the fire pit for cooking. Cell reception is okay in the cabin, wifi is from a Starlink booster!

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
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!

Waterfront Cottage
The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

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

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.

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.

SNOW SWEET, A Yurt for All Seasons
Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.
Popular amenities for kayak rentals in Oakland
House rentals with a kayak

Mirror Pond Cottage

Cozy Waterfront Home With Breathtaking Views!!!

Riverside

Lakefront: Private Hot Tub, Sauna & Free Massages!

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

Beautiful Maine Lakeside Cottage

Modern Lakefront Home w/ Hot Tub • Summer Vacation

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

Lake House on Three Mile Pond with Amazing views

Waterfront Lake House, Kayaks, Fire Pit & Fishing

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Hidden Haven A Rustic Retreat In St. George, Maine

Lake Great Pond| Dog Friendly | Boat Launch

Duck Lane Cottage | Lakefront w/ Dock & Kayaks

Cozy waterfront home on Merrymeeting Bay.

Our charming,oceanfront, Bradford point cottage
Cabin rentals with a kayak

Lakefront Home w/Dock | Porter Lake | Sugarloaf

McKeen's Riverside Retreat

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
Destinations to explore
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec 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 firepit 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
- Belgrade Lakes Golf Club
- Black Mountain of Maine
- Lost Valley Ski Area
- Sugarloaf Golf Club
- Range Ponds State Park





