Vacation rentals in Orland

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Quick stats about vacation rentals in Orland

  • Total vacation rentals

    Explore 160 vacation rentals in Orland

  • Nightly prices starting at

    Orland vacation rentals start at €18 per night before taxes and fees

  • Verified guest reviews

    Over 6,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Orland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Orland rentals

  • 4.9 Average rating

    Orland stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Orland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.
Guesthouse in Orland
4.98 out of 5 average rating, 204 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 800 Mbs fiber internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. We’re very pet friendly!

Top guest favorite
A serene outdoor space features wooden seating facing the lake, surrounded by tall trees. The grassy area leads to a pebble fire pit, creating a cozy gathering spot. The calm water reflects the clear blue sky, enhancing the natural setting.
Home in Ellsworth
4.97 out of 5 average rating, 151 reviews

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.

Top guest favorite
A wooden dock extends into a calm lake, framed by distant hills and clear skies. The water's surface reflects the surroundings, creating a serene and tranquil atmosphere.
Home in Orland
4.98 out of 5 average rating, 124 reviews

Private Lakefront Cottage Close to Bar Harbor

Newly renovated historic lakefront home on 8 acres with a lot of privacy. Conveniently located only 20 minutes from airport, this 2-story cedarshake home sits on the water's edge and is close to Bar Harbor and surrounding picturesque towns for shopping, restaurants and sightseeing. Large wrap-around porch (with dining table that seats 10 and several comfy seating areas) for family fun & outdoor dining. Large deck, perfect for swimming, lake fun and canoe rides. AC and heats in upstairs bedrooms.

Top guest favorite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5 out of 5 average rating, 157 reviews

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

Top guest favorite
A rustic cottage is viewed at sunset, with vibrant hues of orange and pink illuminating the sky. A gravel pathway leads to the entrance, framed by green lawns and decorative flower pots. Trees are visible in the background, enhancing the natural setting.
Guesthouse in Orland
5 out of 5 average rating, 138 reviews

The Greenhouse Cottage

We feel that the best way to describe our getaway to be “Rustic Elegance”. When you walk through the door you will instantly feel the warmth of a uniquely styled Adirondack cottage. Located nearby to the Acadia Highway (aka Route 1), we are close by to historic Fort Knox, Castine, and Acadia. Enjoy our attached “Greenhouse” which has been made over into a delightful screenhouse/patio, the country setting, blueberry fields, and the beautiful sunrises and sunsets! Fire pit, horseshoes, more!!!

Top guest favorite
The charming exterior of a cottage is highlighted by blue wood siding and yellow trim. A flower bed with colorful blooms lines the gravel path leading to the entrance. A decorative birdhouse rests on a tree nearby, complementing the natural surroundings.
Cottage in Surry
4.93 out of 5 average rating, 157 reviews

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.

Top guest favorite
A two-story cabin is nestled among trees, providing a serene natural setting. Adironack chairs are arranged in a circle on the grass, inviting relaxation. A wooden picnic table is visible in the background, offering an outdoor dining option surrounded by lush greenery.
Home in Orland
4.97 out of 5 average rating, 132 reviews

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.

Top guest favorite
A bright living area features two comfortable wicker chairs and a round coffee table, all positioned to take in panoramic waterfront views through large windows. A cozy area rug anchors the space, while a decorative bowl and outdoor binoculars are visible on the table.
Place to stay in Stockton Springs
4.98 out of 5 average rating, 120 reviews

Acadia Region New Oceanfront Cottage

Relax and unwind at this unique waterfront retreat where you can enjoy breathtaking views of the ever-changing tides. Keep an eye out for bald eagles, osprey, and the occasional seal as you soak in the natural beauty around you. This renovated former boathouse combines comfort with convenience, offering the perfect base for your coastal adventures. Situated in Mid Coast, Maine, it's ideally located just an hour from Acadia National Park, 15 minutes from Belfast, and 45 minutes from Camden.

Top guest favorite
A charming cottage is framed by lush green trees and sits along the Penobscot River. The gravel path leads to the entrance, with water visible in the background under a clear blue sky, creating a serene setting for visitors.
Home in Orland
4.97 out of 5 average rating, 148 reviews

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.

Top guest favorite
A serene view of Toddy Pond is framed by a large window. The scene features calm water reflecting the lush greenery and rocks along the shore. A planter filled with colorful flowers sits on the deck, complemented by a single chair positioned for relaxation.
Cottage in Orland
4.97 out of 5 average rating, 63 reviews

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.

Top guest favorite
Cabin in Orland
5 out of 5 average rating, 80 reviews

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

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 451 reviews

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 vacation rentals

When is the best time to visit Orland?

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Frequently Asked Questions

  • How much does it cost to stay in cottage rentals in Orland?

    Experience the best of Orland with our cottage rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Orland?

    Yes! Work meets play with ease at over 40 vacation rentals in Orland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Orland?

    Four-legged friends are welcome in Orland. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Do house rentals in Orland have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Orland. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Orland have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Orland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orland have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Orland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cabin Rentals in Orland?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly cabin rentals in Orland?

    Orland has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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