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

Total vacation rentals
Explore 50 vacation rentals in Orland

Nightly prices starting at
Orland vacation rentals start at G$20,878 GYD per night before taxes and fees

Verified guest reviews
Over 2,830 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Orland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Orland rentals

4.9 Average rating
Orland stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated kayak rentals in Orland
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

Cozy Cottage on the Penobscot – Panoramic Luxury!
Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Coveside Lakehouse on Sandy Point
If you are looking for a beautiful vacation spot on Green Lake, look no further. Cove Side Lake House on Sandy Point is the perfect place for you and your whole family to enjoy the lovely Maine summer, from sunrise until sun set. Whether you enjoy relaxing on the deck, catching a nap in the hammock, or fishing and kayaking, this is the vacation destination you've been dreaming of. Green Lake, located in Ellsworth/Dedham Maine, is a 3,132 acre freshwater lake with a maximum depth of over 170ft.

Tranquil lakefront retreat for nature lovers
Lakefront home with gorgeous views of Springy Pond. Experience the best of Maine living! Enjoy four-season comfort in this home away from home! Idyllic Maine summers, breathtaking fall foliage, or a range of winter activities await. This beautiful house boasts private lake access and spacious grounds, making it a perfect location all year round. You can relax by the fire, or unwind in the hot tub as you create wonderful memories with friends and family. Nightly price includes service charges.

Loon Sound Cottage, On the Water
Loon Sound Cottage, on beautiful Toddy Pond in Surry, is centrally located between Bar Harbor/Acadia & Blue Hill. Come and enjoy the peace and tranquility of a lakeside oasis while just being a short distance from many sites of interest. Visit nearby Castine, Blue Hill, Bar Harbor, and Acadia National Park. Hear the loons at night, kayak to beaver cove and see an eagles nest. A tranquil and peaceful setting. A perfect balance of rest and adventure. We prefer Sat-Sat. rental but flexible.

Waterfront-40min to Acadia-Main House-Kayaks
Lakehouse for those seeking outdoor adventures at Acadia National Park, a relaxing lake trip, or a true historic Maine cabin resort experience. Enjoy a four-season, pet-friendly, Maine lakehouse! The converted Main House at the Getogether Stays cabin micro-resort sleeps 8 and includes WiFi, kayaks, a gas grill, A/C and heat, a picnic table, and Adirondack chairs around the fire pit. The cabin is convenient to Bucksport, Ellsworth, Bangor, and Bar Harbor, making it ideal for exploring Acadia.

Historic Stephenson Farm on 35 acre Mason Pond
This water front historic Stephenson Farmhouse is a cozy 3 bedroom farmhouse that sits on 5 acres with frontage on Lower Mason Pond. A bird lovers paradise along with sightings of beaver & river otters. Trail from house leads to waterfront, canoes, paddles & PFD’s and a picnic table. We’ve maintained the antiquity of the house along with many antique pieces of furniture. Enjoy amazing sunsets, expand your birding life list, pick apples and blueberries in season. . . on a nature preserve.

Lavender by the Sea
The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

Branch Lake Cabin minutes to Acadia (Weekend deal)
Ellsworth is the gateway to Downeast Maine. Just minutes from Acadia National Park, and Bar Harbor, enjoy relaxing along Ellsworth's pristine 9 mile long 120 foot deep Branch Lake, one of Maine's best kept secrets! Our furnished lakeside cottage is a perfect place to vacation in Maine. You won't find a more beautiful or convenient, yet secluded spot, anywhere. Enjoy our kayaks, paddle boards, water mat, fishing equipment, rowboat, & canoe. Swim at our sandy waterfront or relax on shore.

Gran Den Lakefront Home Near Acadia
Gran Den is a large, kid-friendly home on the sunset side of a 9 mi lake (Toddy Pond). Enjoy privacy, stunning elevated sunsets, a dock, raft, canoe, big yard and a tennis court! Deck spans the length of the home - great for grilling, sunbathing, meals, drinks, naps and stargazing. Waterfront and tennis ct only 100 ft from deck. Enjoy all nature offers, loons, bald eagles, humming birds – on a lake that you’ll feel like you own. Close to Acadia National Park, Deer Isle & Blue Hill.

Sea Pearl
This is a Water Front property, unique and tranquil getaway. Newly renovated 2025, this is a perfect spot for your serious fun. Located on water in Penobscot. Bird watchers take notice, watch the eagles soar over head out your door, visit the many islands & see the Puffins, Whale watch. Lots to do kayaking, hiking and lot more! Or just relax in a stunning natural setting on the hammock under the apple trees. Just a short drive to Acadia National Park & Bar Harbor. See you soon.

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.

Graham Lakeview Retreat
Escape to the beauty of coastal Maine in this peaceful and fully-equipped waterfront home—just 40 minutes from Acadia National Park. Enjoy serene water views, launch one of the provided kayaks, or soak in the jacuzzi tub after a day of hiking. Ideal for couples, families, solo travelers, and your four-legged friends, too! Whether you're here for the national park, the coast, or just a quiet escape, this welcoming retreat has everything you need.
Popular amenities for Orland kayak rentals
House rentals with a kayak

The Narrows Lake House/Phillips Lake-Bangor/Acadia

Lakefront Log Cabin on Pleasant Lake

Lake Front-Kayaks-Dock-Fire Pit-Sand Beach-Acadia

A little slice of heaven on Brewer Lake

Gathering Home on Phillips Lake en route to Acadia

Timber Point – Secluded Waterfront Oasis

Oceanfront, Private Beach/Sauna

Toddy Pond Lakehouse-beautiful sunrises &water fun
Cottage rentals with a kayak

Your own private getaway on Pushaw Lake!

Lakefront, near Bar Harbor, ME

Call of the Loon - Water Edge Lake House

Acadia Beach shipwreck cottage Bar Harbor

Lakefront Cottage on Tracy Pond

Mainestay Cottage - 4 Season Waterfront Retreat

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Private Waterfront Home with Kayaks and Firepit
Cabin rentals with a kayak

Bungalow with Swimming Cove

Waterfront Cabin in Hermon

Off Grid Mountain Cabin w/skyline & kayaks

Sunrise Views Cabin with King Bed, Bar & Game Room

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

A-frame cabin by the bay with kayak!

Peaceful 4 season lake house - Pleasant Lake Camp

Rustic Cabin on Beech Hill Pond near Acadia
Destinations to explore
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