Holiday houses in Orland

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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 modern A-frame cabin is showcased with prominent large windows, allowing natural light to fill the interior. Two white adirondack chairs are positioned on the front deck, which is accessed via a set of stairs, surrounded by lush greenery.
Cabin in Brooksville
4.95 out of 5 average rating, 111 reviews

Quiet & relaxing A-Frame in Maine woods “Birch”

Come relax in our newly constructed, 4 season modern A frame on the Blue Hill Peninsula. Located in the beautiful town of Brooksville, only 10 mins from Holbrook Island Sanctuary, 15 minute scenic drive to Blue Hill and Deer Isle/Stonington or 1 hour to Bar Harbor/Acadia National Park. Stocked with everything needed to enjoy a relaxing getaway- EV Charger too! Is the property not available when you need it? “Maple” A Frame is just next door. See separate listing for availability OR to book both.

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
4.99 out of 5 average rating, 192 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 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, 430 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 guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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 out of 5 average rating, 127 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 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, 122 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 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, 140 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 favourite
A charming red cottage exterior is framed by lush greenery and tall trees. Steps lead to the entrance, which features decorative accents and an American flag. Potted plants adorn the porch, adding touches of color to this welcoming entryway.
Cottage in Ellsworth
4.99 out of 5 average rating, 114 reviews

Gateway Cottage Inn Acadia Natl Park Bar Harbor

Keep life simple at this cozy, peaceful and private little "cottage in the woods" that feels more like an Inn with little surprises around every corner. Centrally-located to many attractions such as Acadia National Park, Bar Harbor, Whale Watching, Lobster Fishing tours. Less than 5 minutes from local Ellsworth restaurants, shops, gas stations and supermarkets. The sunroom is perfect for morning coffee, winding down with a glass of wine or curling up with a good book on the boat bed.

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, 117 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 in bedrooms.

Top Guest favourite
A welcoming living area features a stone fireplace and modern furnishings. Two armchairs and a sofa surround a central coffee table, while a dining table is positioned nearby. A large wall-mounted TV is visible, with a well-equipped kitchen in the background.
Apartment in Bucksport
5 out of 5 average rating, 157 reviews

Luxury Coastal Maine 2BR Apt, 2nd Fl Stunning View

The entire building was completely and structurally remodeled and everything is new. Each unit has new floors, walls, lighting, HVAC, kitchens, bathrooms, bedrooms, and brand new mid-century modern furniture throughout. These are truly designed and built as luxury short term rental units. It's location is perfect to explore greater Penobscot Bay region, Acadia National Park, and it sits in the heart of mid-coast Maine. It is beautiful, friendly, and a perfect place to be.

Top Guest favourite
The charming exterior of a Cape Cod-style cottage is displayed, featuring gray siding and white window trims. A red door is centered between two bay windows adorned with planters. An American flag is proudly displayed, and seasonal decorations, including pumpkins, enhance the welcoming entrance.
Home in Verona Island
4.99 out of 5 average rating, 136 reviews

The Ward House

A sunny Maine cottage on a quiet Island sitting on the banks of the east branch of the Penobscot River. 20 miles from Bangor, Belfast, and Ellsworth. 40 miles to Mt. Dessert Island and Acadia National Park. There is room for 7 people. Three beds that sleep two people and one single bed. One bedroom , with a queen size bed, is on the first floor with a small living room. There is a dining room and full kitchen with washer and dryer. The one bathroom is on the first floor.

Guest favourite
A geodesic dome is prominently situated on an elevated deck, surrounded by vibrant fall foliage. The structure showcases a wooden finish, and a small detached building is visible nearby. Clear blue skies add to the serene outdoor setting, providing a peaceful ambiance.
Dome in Ellsworth
4.98 out of 5 average rating, 218 reviews

Nomad's Rest-Secluded Modern Camp 30 miles to MDI

The modern Maine camping experience. Enjoy an unforgettable stay in a geodesic dome outfitted with detached bathroom and shower. A fantastic jumping-off point for your favorite outdoor sports with hiking and biking trails within 10 minutes of the property and 30 miles from Acadia National Park. Return from a day of exploration to views of Maine lakes, the national park and a roaring fire pit! @nomaddomehome on Insta for more pictures.

Top Guest favourite
The cabin exterior is softly illuminated by string lights, enhancing the porch area. A cozy seating arrangement is visible, complemented by a wooden railing and steps leading to the yard. Surrounding trees provide a natural backdrop under the twilight sky.
Cottage in Bucksport
4.98 out of 5 average rating, 161 reviews

Cozy Cottage in the Woods

Our open concept 2 bedroom home nestled in the woods has the charm of a cottage but the comforts of home. Morning coffee on the porch is often accompanied by sightings of deer in the large field out the front door and hummingbirds busy at the feeder. Get away from it all while being only 25 min from Bangor, under an hour from Belfast & Camden, and 45 min to an hour from Acadia & Bar Harbor!

Popular amenities for Orland holiday rentals

When is the best time to visit Orland?

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Avg. price$210 AUD$224 AUD$213 AUD$206 AUD$257 AUD$275 AUD$293 AUD$292 AUD$245 AUD$245 AUD$223 AUD$210 AUD
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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 60 vacation rentals for guests traveling with pets.

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

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

  • Do apartment rentals in Orland have wifi?

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

  • Do cottage rentals in Orland have a bbq area?

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

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

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 40 homes with a bbq area, over 20 homes with self check-in, 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.

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 $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,780 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • 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!

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