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 G$4,184 GYD 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, 210 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!

LocationValueBathroom

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, 127 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.

FamilyValueSleep quality

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
5.0 out of 5 average rating, 164 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

LocationFamilyCheck-in

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
4.96 out of 5 average rating, 154 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.

LocationValueCondition

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
5.0 out of 5 average rating, 26 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.

ValueLocationHospitality

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
5.0 out of 5 average rating, 147 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!!!

FamilyLocationGetting around

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, 138 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.

FamilyLocationBeach

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, 151 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.

LocationValueKitchen

Top guest favorite
Cottage in Ellsworth
4.99 out of 5 average rating, 149 reviews

Gateway Cottage Acadia Natl Park Bar Harbor

Keep life simple at this TINY, cozy, peaceful "cottage in the woods" with little surprises and big charm around every corner. Centrally-located to many attractions such as Acadia National Park, Bar Harbor, Whale Watching and 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.

LocationFamilyLaundry

Top guest favorite
A spacious lakeside deck features two comfortable lounge chairs with red cushions and two Adirondack chairs surrounding a small side table. The serene water reflects soft pastel hues from the sunset, while distant hills create a peaceful backdrop.
Home in Ellsworth
4.99 out of 5 average rating, 155 reviews

Green's Landing on Branch Lake

Welcome to Green’s Landing on Branch Lake, a waterfront retreat on one of Maine’s cleanest lakes. Enjoy two private docks, four kayaks, two paddleboards, a canoe, the Game Barn, fire pit, and room for up to 16 guests. Bring your boat or have one delivered nearby, then spend your days swimming, fishing, and making memories. Just minutes from Acadia National Park, it’s the perfect escape for families and friends.

FamilyLocationHospitality

Top guest favorite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham
4.95 out of 5 average rating, 913 reviews

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

ValueFamilyLong stay

Top guest favorite
The exterior of a two-story house is set against a clear blue sky and surrounded by trees. A spacious lawn features a fire pit with several Adirondack chairs arranged around it, inviting gatherings. The driveway provides access to the house, enhancing its private setting.
Home in Orland
4.96 out of 5 average rating, 116 reviews

Tides' Reach - Private Waterfront King Beds

Twenty-five private acres. Six hundred feet of waterfront. Zero neighbors. Watch the tides from the gourmet kitchen, roast s'mores at the fire pit, explore down to the shore. Bucksport 5 min, Acadia 1 hr, Bangor airport 40 min. Well-behaved dogs welcome

ValueLocationHiking

Popular amenities for Orland vacation rentals

When is the best time to visit Orland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,382 GYDG$31,382 GYDG$34,521 GYDG$30,964 GYDG$41,843 GYDG$45,818 GYDG$43,726 GYDG$43,517 GYDG$36,613 GYDG$36,613 GYDG$33,265 GYDG$31,382 GYD
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 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 house rentals with a dedicated workspace in Orland?

    Yes! Work meets play with ease at over 20 house rentals in Orland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly cabin rentals in Orland?

    Four-legged friends are welcome in Orland. Choose from more than 20 cabin 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 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 Cabin Rentals in Orland?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with wifi, 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.