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 $20 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, 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!

Top guest favorite
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 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.

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, 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.

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, 161 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, 141 reviews

The Greenhouse Cottage

We feel that the best way to describe our getaway to be ā€œRustic Eleganceā€. 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 ā€œGreenhouseā€ 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, 158 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, 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.

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, 121 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
Cabin in Orland
5 out of 5 average rating, 84 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

Guest favorite
A single-story house is positioned amid lush trees with colorful autumn foliage. The gravel driveway leads to a welcoming entrance, while large windows provide glimpses of the surrounding nature. A serene atmosphere is captured with a partly cloudy sky overhead.
Home in Penobscot
5 out of 5 average rating, 34 reviews

Puffin Place

A three acre, restful retreat located on the Blue Hill peninsula. 20-25 minutes to Maine Maritime Academy, 10 minutes to the picturesque town of Blue Hill, 15 minutes to the Penobscot Narrows Bridge and Observatory, and only 45 minutes to Acadia National Park. Puffin Place is equipped with 3 bedrooms (King, Queen, and double bunk beds), a bathroom, full kitchen, comfortable living room, dining area, washer/dryer, internet, and outdoor fire pit.

Superhost
The exterior of a cozy cabin is framed by trees, showcasing a small set of steps leading to the entrance. Beyond the cabin, the serene lake is visible through the foliage, creating a peaceful natural setting.
Cabin in Orland
4.88 out of 5 average rating, 8 reviews

Toddy Pond Sunset Cabin-Stunning views&water fun

This cabin is a lakeside, tree-lined camp retreat on Toddy Pond. Enjoy the pond view and birdsong from your private deck. The open-floor plan offers a queen size main bed, and a combination full and twin bunk for up to 5 people. A kitchenette, full bathroom and dining table are part of the cozy cabin. A few steps through the pines gives you access the small beach and floating dock and a chance to catch your own fish.

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 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.