
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$4,183 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.

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.

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!

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

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.

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!!!

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.

Fish Point Hideaway
Private and charming guesthouse nestled in Mid Coast Maine on the shores of the Orland River. Abundant views of osprey, eagles, seals, and wildlife. Conveniently located approximately 50 minutes from Acadia, 1 hour to Stonington, 30 minutes to Belfast, 20 minutes to Castine and Ellsworth. Local restaurants, shops, grocery store, Alamo Theater, River walk , and events, all within minutes in nearby Bucksport. Come visit the quiet coast and enjoy Maine Vacationland, The Way Life Should Be. “

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!

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.

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.

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.

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
Popular amenities for Orland vacation rentals
Other great vacation rentals in Orland

Toddy Haven: A Lakeside Condo Near Acadia.

Apartment Gateway To Acadia

Legacy Way Vacay

Welcome to The Maine View

Puffin Place

Stall #2 at the Swazey Stable

The Cubby

River Views | Private Hot Tub | The Willow Cabin
When is the best time to visit Orland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,374 GYD | G$31,374 GYD | G$34,511 GYD | G$30,955 GYD | G$41,831 GYD | G$45,805 GYD | G$43,714 GYD | G$43,505 GYD | G$36,602 GYD | G$36,602 GYD | G$33,256 GYD | G$31,374 GYD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°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.
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