
Holiday rentals with a kayak in Cumberland County
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Cumberland County
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Waterfront,Hot tub,Private dock,Freshly renovated
Welcome to the freshly renovated Cabin on a Moose Pond!Nestled near the hills of Pleasant Mountain.Enjoy a day at the lake fishing,swimming,skiing,hiking or snowmobiling. In the evening,relax in the new hot tub,watch a movie on the home theater or challenge friends to video games.End your day by the campfire making s’mores by the pond. Spend a lazy day on the hammock or take a day trip to explore regional attractions in beautiful ME and NH. For your safety, the area is under video surveillance.

Waterfront Gem walkable to Restaurants!
Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Luxury Year-round Treehouse with private hot tub
Skyframe is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Charming Historic Freeport House
Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Beautiful lake-side home close to Portland Maine
A peaceful & charming renovated old home with private dock on Highland Lake, Falmouth Maine, 20 mins from Portland. *Contact us for longer winter availability! **June/July/Aug, Sat-Sat 7 day min Enjoy beautiful sunsets, canoeing, kayaking, paddle-boarding or fishing on the lake. Or take a short drive to downtown Portland, visit Old Port restaurants & bars, local breweries, Freeport outlet shopping, ski resorts, hiking and walking trails, golf courses, indoor/outdoor cinemas, and more!

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Coastal Waterfront Cottage in West Bath
***Please Message me to ask about possible discounts and length of stay minimums.*** 4 season home right on the waters edge on New Meadows River in West Bath sits this newly remodeled home. Fully furnished and includes a Minisplit Heat Pump/ AC, and Propane fireplace. Great location as it is on a dead end road that is just minutes to shopping, restaurants, etc. Incredible spot to watch the boats come and go as Sawyer park boat launch as well as the town boat launch are right in view.

The Loon's Nest Cottage
Located only 30 minutes from Portland this adorable and cozy cottage sits 10 feet from Watchic Lake. Listen to the loons all day, paddle to an island, stare at the glassy lake from the breakfast nook, swim forever, read a book in the screened-in porch or toast marshmallows in the firepit, whichever it may be you'll simply enjoy the peace and tranquility of this very private Maine lake house nestled in the woods. If you’re feeling like a hike, a dinner out there are options a plenty!

Mirror Pond Cottage
A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

Peaceful Cottage on Maine Flower Farm
Maine’s Peaceful Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today
Popular amenities for Cumberland County kayak rentals
Holiday House Rentals with a Kayak

Elevated 4-Season home - Mtn Views +A/C + Firepit

Maine Vacation Home on the Water

The Loons' Nest: Lakefront oasis w/ hottub

Kayak to the Causeway-50s cottage with modern vibe

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

“A Beary Happy Place” stunning home, views & more

Lakehouse/HottubFirePit/2pvtdocks/SUPs/YAKs/LgYard

Brand new Scandinavian cottage: dock & kayaks!
Cottages with a kayak

Highland Lake Beachfront Oasis | Near Portland

Rising Tide Times - quintessential Maine cottage

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Cozy camp near highland lake

Cozy Maine Lakefront Paradise

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Cozy waterfront home on Merrymeeting Bay.

Peaceful Lakeside Maine Retreat
Cabin rentals with a kayak

Idyllic Lakeside Cabin Winter Getaway

Romantic Pond Cabin | 65 Private Acres + Kayak

Amish built cabin on 280 acres near North Conway

Get away at Crystal Lake

Private cabin with lake access, hot tub & firepit!

Modern Forest Cabin w/ Private Hot Tub & Fire Pit

Peaceful and Rustic Lakeside Cabin

Lakefront Maine Retreat~PVT Dock & Year-Round Fun
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Long Sands Beach
- Popham Beach, Phippsburg
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- Scarborough Beach
- Pemaquid Beach
- Footbridge Beach
- Pemaquid Point Lighthouse
- East End Beach
- Cape Neddick Beach
- Coastal Maine Botanical Gardens
- Gooch's Beach
- Popham Beach State Park
- Cranmore Mountain Resort
- King Pine Ski Area
- Hills Beach
- Conway Scenic Railroad
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
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