
Holiday houses in Orland
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Top-rated holiday rentals in Orland
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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!

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.

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 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

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.

Tiny House at Wooded Bliss Homestead
On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

Maine Wilderness Oasis: Hike Swim Kayak Fish
Take it easy at this unique getaway. Spend your days hiking the backyard trails (25 acres behind the house!), swimming or paddle boarding on the lake with a private dock (lake is a 2 minute walk down the driveway!), or traveling to near by coastal towns like Bar Harbor (Bucksport was voted #1 small coastal town in USA!). For dinner, stop by one of the lobster shacks just down the road to bring home your fresh Maine lobster! Come and disconnect (or stay connected if you’re working remotely!).

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.

Waterfront-40min to Acadia-Main House-Fire Place
Enjoy all four of Maine's seasons at this lakehouse. The Main House at Getogether Stays cabin micro-resort sleeps 8 and includes free kayaks. Have you ever dreamed of being the owner of a campground or wondered what it is like to stay in the owner's building at one? Well here is your chance to live your dream for a visit to this cabin campground. The cabins are closed in the winter, but the main house is still available to rent! Enjoy this lovely home and the entire grounds of the property

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

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.

The Reach Retreat
Coastal, light and airy, this studio is perfect for those seeking to explore all that Deer Isle has to offer! Located on the Eggemoggin Reach, you will have access to hiking trails, kayaking, sailing, shopping, and lobsters from the lobster capital of the world, Stonington! We are so lucky to live on this beautiful island and are looking forward to sharing a piece of our paradise with you!
Popular amenities for Orland holiday rentals
Other great holiday rentals in Orland

Carriage House at Bald Hill Cove

Studio on Orland River

Ledgewood Cottage

Lakefront cabin

Maple Cove Camp Lakeside Cottage

Delight<Farmhouse

River Views | Private Hot Tub | The Willow Cabin

Fish Point Hideaway
When is the best time to visit Orland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $227 AUD | $242 AUD | $230 AUD | $222 AUD | $277 AUD | $296 AUD | $316 AUD | $315 AUD | $265 AUD | $277 AUD | $263 AUD | $239 AUD |
| 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
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 $70 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 wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Orland have wifi?
Absolutely! We offer over 50 house rentals with wifi in Orland. Enjoy a tailored experience with all the comforts you desire.
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.
Are there pet-friendly house rentals in Orland?
Four-legged friends are welcome in Orland. Choose from more than 20 house rentals for guests traveling with pets.
Do house rentals in Orland have a bbq area?
Absolutely! We offer over 40 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 50 family-friendly house 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 $30 AUD per night before taxes and fees

Verified guest reviews
Over 6,330 verified reviews to help you choose

Family-friendly holiday rentals
80 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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- Acadia National Park
- Northeast Harbour Golf Club
- Acadia National Park Pond
- Hermon Mountain Ski Area
- Sandy Point Beach
- Dragonfly Farm & Winery
- The Camden Snow Bowl
- Lighthouse Beach
- Sand Beach
- Bear Island Beach
- Eaton Mountain Ski Resort
- Spragues Beach
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Islesboro Town Beach
- Farnsworth Art Museum
- North Point Beach
- Rockland Breakwater Light
- Narrow Place Beach
- Driftwood Beach
- Three Island Beach
- Billys Shore
- Hero Beach
- Pinnacle Park




