
Vacation rentals with a kayak in Oakland
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Oakland

Total vacation rentals
Explore 40 vacation rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 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 kayak rentals in Oakland
Guests agree: these kayak rentals 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)
LocationOutdoor spacesGrill

Lakefront: Private Hot Tub, Sauna & Free Massages!
Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!
LocationValueIndoor spaces

Lakefront Log Cabin on Pleasant Lake
Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch
Outdoor spacesLocationGetting around

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 . Walking trails surround your cabin. Outside there’s 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! & Window A/C
Outdoor spacesValueKitchen

Farm house, River, Island, animals & private Chef.
MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!
Outdoor spacesValueHiking

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.
ValueLocationLayout

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!
Outdoor spacesValueBiking

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!
ValueOutdoor spacesSkiing

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.
Outdoor spacesLocationCheckout

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.
Outdoor spacesLocationAccuracy

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.
LocationValueCheck-in

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.
LocationOutdoor spacesCheck-in
Popular amenities for Oakland kayak rentals
House rentals with a kayak

Modern Lakefront Home w/ Hot Tub • Summer Vacation
ValueLocationHiking

The Modern Lakehouse
ValueOutdoor spacesView

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

Beautiful Maine Lakeside Cottage
ValueLocationParking

Mirror Pond Cottage
LocationOutdoor spacesFamily

Lakeside retreat on quiet cove on Cobbessee Lake!
Outdoor spacesValueComfort

Historic Stephenson Farm on 35 acre Mason Pond
Outdoor spacesLocationPets

Cozy Waterfront Home With Breathtaking Views!!!
ValueOutdoor spacesTV
Cottage rentals with a kayak

Lake Great Pond| Dog Friendly | Boat Launch
LocationOutdoor spacesHiking

Coastal Waterfront Cottage in West Bath
Outdoor spacesValueQuiet

Cozy Lakefront 3 Bedroom 2 bath home on Sand Pond
LocationOutdoor spacesLaundry

Our charming,oceanfront, Bradford point cottage
LocationOutdoor spacesFamily

Cozy waterfront home on Merrymeeting Bay.
ValueLocationNearby

Call of the Loon - Water Edge Lake House
LocationValueGetting around

Waterfront Lake House, Kayaks, Fire Pit & Fishing
Outdoor spacesLocationHeating

Thompson Lake, No Cleaning Fee Pine Point Cottage,
Outdoor spacesValueIndoor spaces
Cabin rentals with a kayak

Lakefront Home with Dock | Porter Lake | Sugarloaf
Outdoor spacesLocationCleanliness

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

Cozy Lakefront Cabin in Freedom, ME
ValueLocationSleep quality

Peaceful & private waterfront cabin
ValueOutdoor spacesRiver

The Getaway- A Cozy Lakeside Cabin
ValueLocationIndoor spaces

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

Webber Pond Cabin LLC
LocationOutdoor spacesPets

The Nest at Camp Skoglund
ValueOutdoor spacesParking
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,043 | ﺩ.ﺇ 900 | ﺩ.ﺇ 914 | ﺩ.ﺇ 1,039 | ﺩ.ﺇ 1,127 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,083 | ﺩ.ﺇ 1,003 | ﺩ.ﺇ 1,043 | ﺩ.ﺇ 1,083 |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Destinations to explore
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- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Saddleback Ski Mountain Maine
- The Camden Snow Bowl
- Rockland Breakwater Light
- Maine Maritime Museum
- 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
- Range Ponds State Park
- Lost Valley Ski Area
- Sugarloaf Golf Club





