
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 ﺩ.ﺇ 367 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.

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.

Private Waterfront Home with Kayaks and Firepit
Retreat to your own coastal oceanfront paradise, where each day begins with breathtaking views. A private boardwalk leads to your secluded beach — perfect for morning strolls, exploring tidal pools, or launching kayaks into sparkling waters. Evenings bring fireside marshmallows under the stars with waves as your soundtrack. Whether you seek adventure with scenic drives to Acadia National Park or quiet mornings with coffee, sea breezes, and seabirds, this is where comfort meets Maine’s coast.

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.

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.

Romantic Lakeside Cottage - Fireplace - To Acadia
The cottage is new, directly on the water and the perfect romantic getaway for two. Come escape, relax and spend time in a peaceful setting amid trees and rock gardens. The cottage is located on Toddy Pond in Orland, Maine. Toddy Pond is a large lake (9+ miles long) and located between Ellsworth and Bucksport. The cottage is only 50 feet from the water's edge Use of a canoe and kayaks is included. Bar Harbor and Acadia National Park are about 45 minutes away and perfect day trip.

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.

Waterfront Retreat | Dock, Kayaks & Outdoor Movies
You didn’t know you needed this- until you arrived. A modern studio tucked right on the water’s edge, where nothing is between you and the lake but loons, sunlight, and time to relax. Private dock (float, fish, float again) Spa-style indoor + outdoor showers (yes, both. Why not?) Outdoor movie night under a blanket of stars Pet-friendly Swimming, stargazing, and stories you’ll be telling next year Just a short drive to town or Acadia — if you ever want to leave.

Magical Lakefront Cabin on 5 Acres-25 Mi to Acadia
Enjoy a truly immersive experience in our unique open air lakefront cabin. The expansive screen windows allow you to lounge in comfort and feel the fresh air as you experience the birds chirping, loons calling, and frogs singing at night. On chilly nights, draw the curtains and light the gas fireplace for a cozy evening you'll never forget. Relax in a hammock, hike the trails, enjoy kayaking, paddleboarding, swimming or fishing on our peaceful lake. 40 min. to Acadia

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.
Popular amenities for Orland kayak rentals
House rentals with a kayak

Lakefront Log Cabin on Pleasant Lake

Waterfront| Hot Tub| Fire Pit|King Bed|Near Acadia

Schoodic Loft Cabin "The Roost" with Kayaks

Water's Edge-Oceanfront with Stellar View

Historic Stephenson Farm on 35 acre Mason Pond

Green's Landing on Branch Lake

Tranquil lakefront retreat for nature lovers

The Narrows Lake House/Phillips Lake-Bangor/Acadia
Cottage rentals with a kayak

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Acadia Beach shipwreck cottage Bar Harbor

Mainestay Cottage - 4 Season Waterfront Retreat

Your own private getaway on Pushaw Lake!

Lakefront Cottage on Tracy Pond

Modern RV on Tracy Pond

Lakefront, near Bar Harbor, ME

Call of the Loon - Water Edge Lake House
Cabin rentals with a kayak

Lakefront Cottage/Private Midcoast Maine

Bear Cabin, Acadia, Downeast Maine, Lake Access

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

Sunrise Views Cabin with King Bed, Bar & Game Room

Lakefront Cabin in Acadia National Park

Waterfront Cabin in Hermon

Cozy Lakefront Cabin close to Acadia National Park

Bungalow with Swimming Cove
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