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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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Home in Stetson

4.96 out of 5 average rating, 174 reviews

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Guest suite in Orrington

4.97 out of 5 average rating, 105 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 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.

Cottage in Trenton

4.97 out of 5 average rating, 331 reviews

NEW Whitetail Cottage, Acadia National Park 7m

NEW Whitetail Cottage East only 6.9 mi to Acadia National Park Maine - a hikers paradise! Centrally located for a perfect Acadia Adventure! Book for the convenient location - stay for the style. Tiny home has WIFI & SMART TV. Off the main(e) drag but nestled in a wooded property 1/2 mile from Bar Harbor Rd/Route 3 down the road from Mount Desert Island and a stones throw from multiple authentic Maine lobster pounds. Perfect for 2 . A short drive to MDI, Acadia, Bar Harbor,Southwest Harbor

Guesthouse in Orland

4.99 out of 5 average rating, 137 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!

Yurt in Appleton

4.96 out of 5 average rating, 216 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

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.

Home in Bucksport

4.96 out of 5 average rating, 125 reviews

Lake Front-Maine Themed-Soaking Tub-Fire Pit-Kayak

Brand new year-round lake house is perfect for the outdoor recreational enthusiast visiting Acadia National Park, the work-from-home adventurist, a big family lake house trip, or a cold-weather spa escape. Enjoy this spacious waterfront home in Bucksport, Maine. Relax in the soaking tub, fish and paddle the lake, or work remotely with a view. When you want to explore, the home's location is convenient to Bangor, Brewer, Ellsworth, and Bar Harbor!

Rental unit in Ellsworth

4.94 out of 5 average rating, 290 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!

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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

5 out of 5 average rating, 36 reviews

Sail Loft

Cottage in Surry

4.84 out of 5 average rating, 62 reviews

Beautiful Maine Retreat: 3 Bdrm Lakeside Cottage

Home in Verona Island

4.96 out of 5 average rating, 81 reviews

Vernon's View

Tiny home in Bangor

4.84 out of 5 average rating, 25 reviews

Field of Dreams Tiny Home

Cabin in Bar Harbor

5 out of 5 average rating, 57 reviews

New Modern Cabin with RV Pad near Acadia

Home in Orland

4.88 out of 5 average rating, 40 reviews

Sun House Acadia

Cabin in Jackson

4.99 out of 5 average rating, 84 reviews

Wall of windows w/ forest views

Cabin in Northport

4.94 out of 5 average rating, 34 reviews

Bayside Island View Log Cabin, with Beach Access

Quick stats about vacation rentals in Orland

Total rentals
110 properties
Nightly prices starting at
G$4,180 GYD 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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