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Holiday houses in Orland

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Top-rated holiday rentals in Orland

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

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Apartment in Searsport

4.82 out of 5 average rating, 291 reviews

Lakefront Vacation Apartment in Searsport ME

All season private top floor apartment. Hammock, loungers, floats. Acadia/State parks close. Canoe, kayaks, hot tub/wood floating dock (seasonal use), fire pit, grill, swim, fish. Modern/Antique furnished: queen bed plus loveseat twin. Massage/lounger. 2nd queen, twin inflatables. Fully equipped kitchen. Families w/kids, business guests welcome. Wifi smart TV. Great hikes, mountain bike rentals close. Snow shoes/sled included, skiing close. Separate entrance/apt above home not full home.

17–24 Nov

$189 NZD per night

Guest favourite

Guesthouse in Bucksport

4.92 out of 5 average rating, 278 reviews

Chateau Chouinard Acadia NP & MMA, pets okay!

Contactless entry. Central location between Belfast, Bangor and Ellsworth. Close to Fort Knox and the Bucksport river walk, schools, restaurants and the business district. Just 50 minutes to Acadia National Park. Our casual, clean environment can be a place for you to relax and enjoy your stay in mid coast Maine at the gateway to the down east. There is a heat pump providing both heat and air conditioning, fireplace and outdoor firepit. Full kitchen with spices and breakfast items included.

1–8 Jan

$295 NZD per night

Guest favourite

Guesthouse in Orland

5.0 out of 5 average rating, 74 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!!!

21–28 Dec

$291 NZD per night

Guest favourite

Home in Orland

4.97 out of 5 average rating, 75 reviews

Lakefront Cottage Close to Bar Harbor on 8 acres

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 dock, perfect for swimming and lake fun. Canoes and other equipment available for use.

14–21 Sep

$713 NZD per night

Guest favourite

Guesthouse in Prospect

4.97 out of 5 average rating, 116 reviews

The Penobscot River Ranch Guesthouse

This unique four season property sits on 13+ acres on the Penobscot River in Prospect Maine facing Winterport. 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.

11–18 Jun

$185 NZD per night

Guest favourite

Cottage in Surry

4.92 out of 5 average rating, 128 reviews

Loon Sound Cottage, On the Water

Loon Sound Cottage, on beautiful Toddy Pond in Surry, is centrally located between Bar Harbor/Acadia & Blue Hill Peninsula. 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 wonderful place for the perfect balance of rest and adventure.

21–28 Sep

$513 NZD per night

Guest favourite

Guesthouse in Orland

4.99 out of 5 average rating, 103 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!

29 Oct – 5 Nov

$205 NZD per night

Guest favourite

Tiny home in Blue Hill

4.94 out of 5 average rating, 155 reviews

New enchanting retreat near Acadia National

The camp is brand new on 27 acres of land 3 min to Blue Hill Mountain and 5 min to Blue Hill downtown which is right on the water of The Blue Hill Bay. This is an edge wood enchanting retreat perfect for two to hear birds, squirrels and porcupines. Remember to pick some blueberries when it is in season before the black baby bear down the road eat them all. 3D nature is unfolding right in front of your eyes and Acadia National Park is 50 min drive from here. Oh man, you are free! 编辑

20–27 Feb

$244 NZD per night

Guest favourite

Home in Orland

5.0 out of 5 average rating, 10 reviews

New! Waterfront! Main House at Lakeside Campground

NEW! We'd love to host you and get your feedback on our newest listing. 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. Though the cabins closed up for the winter, the main house is still available to rent! During the summer, everything will be available for rent. Enjoy this lovely home and the entire grounds of the property.

20–27 Jan

$354 NZD per night

Guest favourite

Guesthouse in Penobscot

4.99 out of 5 average rating, 166 reviews

Sea Pearl

Take it easy at this unique and tranquil getaway. Newly renovated, this is a perfect spot for your serious fun. Located right on water of the Northern Bay in Penobscot. The Northern Bay is considered the hidden Gem of the bay. This area of the bay is tidal. Come watch the eagles soar over head Just out your door. Kayaking, sailing, hiking, seafood , and lot more! Or just relax in a stunning natural setting. Just a short drive to Acadia National Park, & Bar Harbor.

1–8 Sep

$359 NZD per night

Guest favourite

Dome in Ellsworth

5.0 out of 5 average rating, 139 reviews

Nomad's Rest-Secluded Modern Camp 30 miles to MDI

The modern Maine camping experience. Enjoy an unforgettable stay in a geodesic dome outfitted with detached bathroom and shower. A fantastic jumping-off point for your favorite outdoor sports with hiking and biking trails within 10 minutes of the property and 30 miles from Acadia National Park. Return from a day of exploration to views of Maine lakes, the national park and a roaring fire pit! @nomaddomehome on Insta for more pictures.

21–28 Sep

$516 NZD per night

Guest favourite

Campsite in Penobscot

4.98 out of 5 average rating, 107 reviews

Private Lakeside Camping in Penobscot, Maine

Private lakeside camping on Toddy pond in Penobscot, Maine 50 min. from Acadia and Bar Harbor. This 400 foot private wooded lakeside lot is available for camping. This rental is close to Acadia, Ellsworth, Bucksport and the Blue Hill Peninsula. Go out and explore the area attractions or stay put and swim, fish, and kayak on one of Downeast Maine's most popular lakes; Toddy Pond.

22 Feb – 1 Mar

$246 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Popular amenities for Orland holiday rentals

Free parking on premises

Air conditioning

Stay near Orland's top sights

Carrier's Mainely Lobster22 locals recommend

Crosby's Drive-In13 locals recommend

Glenn's Place14 locals recommend

Great Pond Mountain Wildlands, Dead River Trailhead12 locals recommend

Big Chicken Barn33 locals recommend

Bucksport Golf Club4 locals recommend

Other great holiday rentals in Orland

Guest favourite

Cabin in Orland

5.0 out of 5 average rating, 15 reviews

Magical Lakefront Cabin on 5 Acres-25 Mi to Acadia

30 Mar – 6 Apr

$1,003 NZD per night

Guest favourite

Cottage in Orland

4.95 out of 5 average rating, 42 reviews

Romantic Lakeside Cottage - Fireplace - To Acadia

16–23 Jun

$498 NZD per night

Guest favourite

Chalet in Orland

4.96 out of 5 average rating, 74 reviews

Rocky Haven: Tranquil Lakeside Cottage Near Acadia

15–22 Oct

$707 NZD per night

Home in Orland

4.88 out of 5 average rating, 8 reviews

Gully Brook Cottage! Lake Access!

22–29 May

$599 NZD per night

Guest favourite

Home in Orland

4.94 out of 5 average rating, 16 reviews

Sun House Acadia

20–27 Oct

$808 NZD per night

Guest favourite

Home in Orland

4.98 out of 5 average rating, 44 reviews

Tides' Reach - Private Waterfront King Beds

17–24 May

$626 NZD per night

Guest favourite

Cottage in Dedham

4.93 out of 5 average rating, 90 reviews

My Blue Heaven

15–22 Dec

$254 NZD per night

Guest favourite

Cabin in Bucksport

4.99 out of 5 average rating, 97 reviews

The Sunset Chalet | PERFECT Location!

4–11 Jan

$1,164 NZD per night

Quick stats about holiday rentals in Orland

Total rentals
100 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
$34 NZD before taxes and fees

Destinations to explore