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Vacation rentals in Orland

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Top-rated vacation rentals in Orland

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

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Guest suite in Orrington

4.97 out of 5 average rating, 104 reviews

Lake front luxury retreat with an Island View

Indulge in lakeside luxury at our modern, waterfront studio retreat! Perched on the water's edge, this pet-friendly haven offers: Private dock and lake access · Spa-inspired indoor and outdoor showers · Cozy fire pit for a relaxing movie night under the stars · Unbeatable views and direct access to the lake for swimming & soaking up the sun · The serene sounds of loons and unforgettable memories to cherish. A short drive from town, experience the best of Maine living in style and tranquility.

Cabin in Eastbrook

4.96 out of 5 average rating, 241 reviews

Hemlock Cabin.

Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scammons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

Cottage in Trenton

4.98 out of 5 average rating, 586 reviews

Whitetail by the River, Acadia National Park 10m

Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Now with WiFi! Tiny home is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature.Enjoy privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. A short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Northeast Harbor,Shops & Lobster Pounds

Guesthouse in Prospect

4.97 out of 5 average rating, 124 reviews

The Penobscot River Ranch Guesthouse

This unique four season property sits across from conservation land on the Penobscot River in Prospect Maine. There is a 1/2 mile trail down to the river, great for hiking and snowshoeing. An awesome place to unwind with easy access for exploring mid coast and Downeast Maine. Less than 10 minutes to Rt 1 and The Penobscot Narrows Bridge and Rt 1A, 18 miles to Belfast, Castine, Blue Hill, Ellsworth. About an hour to Acadia NP and 45 min to Bangor. Great views of the land, river and wildlife.

Cottage in Dedham

4.93 out of 5 average rating, 103 reviews

My Blue Heaven

The cabin is totally renovated with new appliances. Very cute and cozy, perfect for couples looking for a romantic get away. Jenkins Beach is closed for renovations this summer but you can still rent/launch boats there for a small fee. The cabin has WiFi and two TV’s, one has Apple TV, the other has streaming services as well and both have DVD players. Our cabin is not childproof, so not suitable for children under 5. Please look closely at the pictures if you’re bringing a small child.

Guesthouse in Orland

4.99 out of 5 average rating, 136 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 400 Mbs cable 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. Pet friendly!

Guest suite in Mount Desert

4.97 out of 5 average rating, 215 reviews

Otter Creek Retreat hosted by Elaine & Richard

Between Bar Harbor and Seal Harbor, 10 minutes by car to both and just 5 minutes by car to the Otter Cliff entrance to Acadia Park Loop Road. Walk to the Causeway via the Grover Path in 15 minutes. 5-minute walk to the Cadillac South Ridge Trail. Large high-ceiling studio with private parking and entrance with beautiful sheltered second-story deck. We are on the Blackwoods/Bar Harbor bus route so you can catch the free Island Explorer LL Bean buses to Bar Harbor and back.

Guesthouse in Ellsworth

4.89 out of 5 average rating, 103 reviews

Large adorable 1 bedroom loft with ocean frontage

What you will love - Modern living space - Ocean Access - Frontage on Union River - Close to everything - but seems like you are in the woods. - Abundant wildlife - Store within walking distance - Outdoor deck on river - Views of Ellsworth Harbor - Full kitchen and laundry - Full bath and Half bath for guests - Air conditioning - Upscale Contemporary Decor - Situated on a 10 acre lot, with large lawn, pond, and within a 2 minute drive to downtown Ellsworth Maine.

Guest suite in Orono

4.99 out of 5 average rating, 495 reviews

Private Studio in the Heart of Orono

Slip into the comforts of a private, clean, and modern suite. A plush mattress, crisp white linens, granite countertops, and a rain shower. Walking distance to many of Orono's microbreweries and restaurants. Four minutes to UMaine campus (1 mile), 10 minutes to Bangor, 1 hour and 20 minutes to Acadia National Park/Bar Harbor. *The building next door is undergoing renovations. Guests may hear some light construction noise Mon-Fri during normal working hours.*

Rental unit in Ellsworth

4.94 out of 5 average rating, 289 reviews

Coastal Studio in Ellsworth

This comfortable, furnished, studio apartment is only 30 minutes to Acadia National Park. Come enjoy a peaceful destination with beautiful, distant views of the mountains. Includes some outdoor living with your own fire pit area, a bundle of wood, and a propane grill. Sleeping arrangements include 2 queen size beds and/or Pack N Play. We are pet friendly, but ask that you notify us if you are bringing your pet.

Cottage in Waltham

4.95 out of 5 average rating, 745 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

Cottage in Hampden

4.99 out of 5 average rating, 274 reviews

MaineStay Cottage #5 Full Kitchen Hampden/Bangor

Welcome to MaineStay Cottage #5 highlighting a bright and airy living space with unique Maine touches throughout. Featuring a remodeled fully stocked kitchen, an electric fireplace, a smart TV for streaming your favorite shows, with a charming dining area for 2, a comfortable queen size bed, and everything you’d need for a relaxing stay - you can’t go wrong!

Vacation rentals for every style

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Stylish accommodations and amenities

Popular amenities for Orland vacation rentals

Laptop-friendly workspace

Stay near Orland's top sights

Big Chicken Barn33 locals recommend

Hannaford Supermarket25 locals recommend

Carrier's Mainely Lobster22 locals recommend

Glenn's Place14 locals recommend

Crosby's Drive-In13 locals recommend

Great Pond Mountain Wildlands, Dead River Trailhead12 locals recommend

Other great vacation rentals in Orland

Home in Belfast

4.88 out of 5 average rating, 43 reviews

Belfast Ocean Breeze

Home in Verona Island

4.96 out of 5 average rating, 81 reviews

Vernon's View

Tiny home in Bangor

4.91 out of 5 average rating, 23 reviews

Field of Dreams Tiny Home

Home in Bucksport

4.91 out of 5 average rating, 87 reviews

Maine Wilderness Oasis: Hike Swim Kayak Fish

Rental unit in Bucksport

4.87 out of 5 average rating, 23 reviews

Extended Stay Apt 3

Rental unit in Bucksport

4.97 out of 5 average rating, 31 reviews

The Cubby

Home in Orland

4.98 out of 5 average rating, 62 reviews

Tides' Reach - Private Waterfront King Beds

Home in Orland

5 out of 5 average rating, 24 reviews

Fish Point Hideaway

Quick stats about vacation rentals in Orland

Total rentals
110 properties
Nightly prices starting at
R362 ZAR before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

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.
How much does it cost to stay in house rentals in Orland?
Experience the best of Orland with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Cottage Rentals in Orland?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Orland have wireless internet?
Absolutely! We offer over 30 house rentals with wireless internet in Orland. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Orland have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Orland. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly cabin rentals in Orland?
Four-legged friends are welcome in Orland. Choose from more than 10 cabin rentals for guests traveling with pets.
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.
Are there family-friendly house rentals in Orland?
Orland has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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