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Holiday houses in Orland

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Orland

  • Total holiday rentals

    Explore 160 holiday rentals in Orland

  • Nightly prices starting at

    Orland holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Orland holiday 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 holiday rentals in Orland

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

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Top Guest favourite
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, 206 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!

LocationFamilyLaundry

Top Guest favourite
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, 125 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.

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Top Guest favourite
A cozy outdoor seating area features multiple wooden chairs arranged around a stone fire pit, nestled in a grassy clearing. The cottage with large windows and wooden accents is visible in the background, surrounded by tall trees, creating a serene natural setting.
Home in Orland
5.0 out of 5 average rating, 22 reviews

Sunset Cove Cottage

This isn’t just another rental house - This is an experience! Book your stay at the Beautiful and Majestic Sunset Cove Cottage! Step into a little slice of Heaven nestled near the beautiful shores of Toddy Pond in coastal Maine. Incredibly crafted Post and Beam cottage with live edge details along side modern features. Come with friends, family, or a secluded couples trip and enjoy the private sand beach, the quiet cottage settings, and the local attractions that only Downeast Maine can offer.

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Top Guest favourite
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
5.0 out of 5 average rating, 139 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!!!

ValueFamilyNearby

Top Guest favourite
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.

LocationFamilyBreakfast

Guest favourite
A well-equipped kitchen features light wood cabinetry and ample counter space. A ceiling fan provides airflow, while natural light filters in through a window. An island with a sink is centrally located, and modern appliances are neatly arranged for convenience.
Apartment in Verona Island
4.92 out of 5 average rating, 26 reviews

Apartment Gateway To Acadia

This amazing 1 bedroom apartment is situated on the edge of Penobscot Bay. Beautiful Morning View of the Sun rising over the bay & the meticulously cared for lawn. The property is centrally located only 38 Mi to Acadia National Park, 17 m to Belfast, 21 M to the waterfront concerts Bangor & many other locations. It is spacious, incredibly clean & very well equipped.Features a large kitchen, outdoor seating w a beautiful view.A region full of amazing restaurants, history & famous lobster rolls!

ValueLocationHospitality

Guest favourite
A serene sunset over Toddy Pond is captured, with vibrant colors reflecting on the calm water. Large rocks and patches of grass are visible along the shoreline, framed by trees in the background, creating a tranquil atmosphere in nature.
Home in Ellsworth
5.0 out of 5 average rating, 11 reviews

Sunset Cove Lakeside

Discover the perfect getaway at our charming cottage, nestled on the tranquil shores of Toddy Pond. Enjoy exclusive access to your private beach, steps from the cottage. Explore the beauty of the area with nearby hiking trails, charming shops, and delightful restaurants. Easy day trips to many coastal peninsulas including Acadia National Park. Seeking a peaceful retreat or an adventure-filled vacation? Our cottage offers the perfect blend of comfort and nature. Unforgettable memories await!

FamilyLocationAmenities

Top Guest favourite
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, 135 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.

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Top Guest favourite
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.

LocationFamilyCondition

Top Guest favourite
Cabin in Orland
5.0 out of 5 average rating, 83 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

LocationFamilyDecor

Top Guest favourite
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, 452 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.

ValueLocationLong stay

Top Guest favourite
A cozy seating area is positioned in front of large windows, offering views of the bay. Two velvet armchairs and a round table are adorned with a floral arrangement. Natural light illuminates the space, creating a serene atmosphere.
Apartment in Bucksport
5.0 out of 5 average rating, 92 reviews

Bayside view

I would like to welcome you to a spacious yet cozy, luxury bayside apartment. This 2 bedroom, 1 bath can sleep 6. Two comfy queen beds, a daybed with trundle on the cantilevered sunroom with breathtaking view. You are a short 30 minute ride from many locations that are popular here in Maine. Also a beautiful 45 to 60 minutes ride down Coastal Route 1, brings you to places like Acadia National Park, Bar Harbor, Camden, Rockport, & Rockland.

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Popular amenities for Orland holiday rentals

When is the best time to visit Orland?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$255 NZD$255 NZD$281 NZD$252 NZD$340 NZD$373 NZD$356 NZD$354 NZD$298 NZD$298 NZD$271 NZD$255 NZD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Frequently Asked Questions

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

    Experience the best of Orland with our apartment rentals, starting at about $60 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 cabin rentals in Orland have wifi?

    Absolutely! We offer over 20 cabin 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 house rentals in Orland?

    Orland has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.