
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 $154 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.

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!
ValueOutdoor spacesAir conditioning

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)
LocationValueBackyard

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
ValueLocationDecor

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!!!
ValueLocationNearby

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.
Outdoor spacesLocationFamily

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 spacesLocationGetting around

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!
LocationValueAmenities

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.
ValueLocationCleanliness

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.
LocationOutdoor spacesCleanliness

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.
LocationValueHeating

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 spacesCondition

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.
ValueLocationTV
Popular amenities for Oakland kayak rentals
Holiday House Rentals with a Kayak

Mirror Pond Cottage
Outdoor spacesLocationNearby

The Loons' Nest: Lakefront oasis w/ hottub
LocationOutdoor spacesCheckout

Cozy Waterfront Home With Breathtaking Views!!!
Outdoor spacesValueHiking

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

Beautiful Maine Lakeside Cottage
ValueLocationCleanliness

Modern Lakefront Home w/ Hot Tub • Summer Vacation
Outdoor spacesValueHospitality

Lakefront Log Cabin on Pleasant Lake
Outdoor spacesLocationFamily

Lakeside retreat on quiet cove on Cobbessee Lake!
ValueOutdoor spacesBarbecue
Cottages with a kayak

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

Thompson Lake, No Cleaning Fee Pine Point Cottage,
Outdoor spacesValueCleanliness

Coastal Waterfront Cottage in West Bath
Outdoor spacesLocationCleanliness

Hidden Haven A Rustic Retreat In St. George, Maine
Outdoor spacesValueKitchen

Cozy waterfront home on Merrymeeting Bay.
Outdoor spacesValueHospitality

Our charming,oceanfront, Bradford point cottage
ValueOutdoor spacesGetting around

Cozy Lakefront 3 Bedroom 2 bath home on Sand Pond
LocationValueBiking

Loons Rest – Maine Quintessential Cottage
Outdoor spacesLocationAmenities
Cabin rentals with a kayak

Lakefront Home with Dock | Porter Lake | Sugarloaf
Outdoor spacesLocationShared spaces

The Getaway- A Cozy Lakeside Cabin
Outdoor spacesValueHeating

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

Rustic, cozy cabin on Sebago Lake. A hidden gem.
LocationValueCondition

Peaceful & private waterfront cabin
LocationOutdoor spacesHot tub

Maine Belgrade Lakes Waterfront - Great Pond
LocationValueGetting around

Modern lakefront log cabin with sunset views.
Outdoor spacesLocationQuiet

Cozy Lakefront Retreat
LocationOutdoor spacesBreakfast
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $512 NZD | $512 NZD | $485 NZD | $418 NZD | $425 NZD | $483 NZD | $524 NZD | $512 NZD | $503 NZD | $466 NZD | $485 NZD | $503 NZD |
| 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
- Montreal Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Bar Harbor Holiday rentals
- Salem Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- The Hamptons Holiday rentals
- 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





