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Family-friendly vacation rentals in Orland

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Quick stats about vacation rentals that are family-friendly in Orland

  • Total vacation rentals

    Explore 100 vacation rentals in Orland

  • Nightly prices starting at

    Orland vacation rentals start at G$27,198 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,580 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Orland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Orland rentals

  • 4.9 Average rating

    Orland stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Orland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.
Guesthouse in Orland

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!

Indoor spacesKitchenBackyard

4.98 out of 5 average rating, 213 reviews
Top guest favorite
A wooden dock extends into a calm lake, framed by distant hills and clear skies. The water's surface reflects the surroundings, creating a serene and tranquil atmosphere.
Home in Orland

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.

FamilyKitchenLaundry

4.98 out of 5 average rating, 127 reviews
Top guest favorite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden

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

KitchenIndoor spacesCondition

5.0 out of 5 average rating, 169 reviews
Top guest favorite
A rustic cottage is viewed at sunset, with vibrant hues of orange and pink illuminating the sky. A gravel pathway leads to the entrance, framed by green lawns and decorative flower pots. Trees are visible in the background, enhancing the natural setting.
Guesthouse in Orland

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!!!

FamilyKitchenLocation

5.0 out of 5 average rating, 150 reviews
Top guest favorite
A two-story cabin is nestled among trees, providing a serene natural setting. Adironack chairs are arranged in a circle on the grass, inviting relaxation. A wooden picnic table is visible in the background, offering an outdoor dining option surrounded by lush greenery.
Home in Orland

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.

KitchenIndoor spacesHiking

4.97 out of 5 average rating, 140 reviews
Top guest favorite
A charming cottage is framed by lush green trees and sits along the Penobscot River. The gravel path leads to the entrance, with water visible in the background under a clear blue sky, creating a serene setting for visitors.
Home in Orland

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.

KitchenIndoor spacesParking

4.97 out of 5 average rating, 153 reviews
Top guest favorite
A lakeside view showcases a cottage surrounded by tall trees, with a wooden deck featuring large windows. Colorful kayaks and a canoe rest on the shore near a sandy waterfront, reflecting the serenity of the calm water.
Cottage in Ellsworth

Peaceful Branch Lake Cabin minutes to Acadia

Ellsworth is the gateway to Downeast Maine. Just minutes from Acadia National Park, and Bar Harbor, enjoy relaxing along Ellsworth's pristine 9 mile long 120 foot deep Branch Lake, one of Maine's best kept secrets! Our furnished lakeside cottage is a perfect place to vacation in Maine. You won't find a more beautiful or convenient, yet secluded spot, anywhere. Enjoy our kayaks, paddle boards, water mat, fishing equipment, rowboat, & canoe. Swim at our sandy waterfront or relax on shore.

Indoor spacesKitchenHospitality

4.88 out of 5 average rating, 113 reviews
Guest favorite
A contemporary wooden home is nestled among tall trees, with a spacious deck extending from the entrance. The natural surroundings and large windows offer scenic views of the lake, creating a serene setting for relaxation.
Home in Surry

Gran Den Lakefront Home Near Acadia

Gran Den is a large, kid-friendly home on the sunset side of a 9 mi lake (Toddy Pond). Enjoy privacy, stunning elevated sunsets, a dock, raft, canoe, big yard and a tennis court! Deck spans the length of the home - great for grilling, sunbathing, meals, drinks, naps and stargazing. Waterfront and tennis ct only 100 ft from deck. Enjoy all nature offers, loons, bald eagles, humming birds – on a lake that you’ll feel like you own. Close to Acadia National Park, Deer Isle & Blue Hill.

FamilyIndoor spacesLong stay

4.94 out of 5 average rating, 181 reviews
Top guest favorite
A modern cabin is set against a backdrop of tall pine trees, featuring large windows that invite natural light. The exterior showcases a wooden deck with a seating area, complemented by a staircase leading to the entrance.
Cabin in Penobscot

Modern Cabin in the Pines • Hot Tub + Near Acadia

Enjoy our cozy home-away-from-home amid towering pines and granite boulders — the perfect respite after exploring Acadia. Our newly built cabin has rustic Maine charm and modern comforts: AC, waterfall shower, memory foam mattresses, indoor gas fireplace, outdoor gas fire pit, gas grill, hot tub, 4KTV, high-speed internet, modern kitchen, filtered water, gas range, high-end appliances, and front-loading washer/dryer.

FamilyIndoor spacesCheckout

4.97 out of 5 average rating, 191 reviews
Top guest favorite
A spacious lakeside deck features two comfortable lounge chairs with red cushions and two Adirondack chairs surrounding a small side table. The serene water reflects soft pastel hues from the sunset, while distant hills create a peaceful backdrop.
Home in Ellsworth

Green's Landing on Branch Lake

Welcome to Green’s Landing on Branch Lake, a waterfront retreat on one of Maine’s cleanest lakes. Enjoy two private docks, four kayaks, two paddleboards, a canoe, the Game Barn, fire pit, and room for up to 16 guests. Bring your boat or have one delivered nearby, then spend your days swimming, fishing, and making memories. Just minutes from Acadia National Park, it’s the perfect escape for families and friends.

FamilyIndoor spacesGrill

4.99 out of 5 average rating, 158 reviews
Guest favorite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham

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

FamilyIndoor spacesHospitality

4.94 out of 5 average rating, 921 reviews
Top guest favorite
A spacious living area features vaulted wood ceilings and large windows offering views of the lake. A cozy sectional sofa and a red accent chair are arranged around a patterned rug. A wooden dining table is positioned nearby, enhancing the open layout.
Cabin in Bucksport

The Sunset Chalet | PERFECT Location!

Cozy lakefront cottage nestles in nature with private water access on beautiful Hancock Pond. Only 35 miles (45-60 minute drive) to Bar Harbor & Acadia National Park. Comfortably furnished with all the conveniences of home! Includes a dock, fire pit, and two kayaks. ***We are Dog Friendly!***

Indoor spacesKitchenBeach

4.99 out of 5 average rating, 138 reviews

Popular amenities for Orland family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A charming off-grid cabin stands amidst lush greenery, featuring large front windows framed by wooden trim. A picnic table with potted flowers occupies a gravel area in front, inviting outdoor gatherings. Solar panels are visible on the roof, showcasing eco-friendly energy use.
Place to stay in Owls Head

A comforting sweet off grid cabin near the beach!

FamilyIndoor spacesBeach

4.98 out of 5 average rating, 311 reviews
Guest favorite
A charming lakefront home showcases large windows and a spacious deck. The exterior features a mix of green siding and natural stone pathways, with a fire pit surrounded by seating. Nearby, seasonal foliage adds vibrant color to the serene landscape.
Home in Otis

Tranquil lakefront retreat for nature lovers

KitchenFamilyAccess

4.95 out of 5 average rating, 108 reviews
Guest favorite
Home in Penobscot

Delight<Farmhouse

KitchenIndoor spacesAir conditioning

4.91 out of 5 average rating, 130 reviews
Top guest favorite
The cabin's exterior features a colorful mural along one side, complemented by large windows. A spacious deck is furnished with black rocking chairs and a small table, surrounded by natural landscaping and gravel pathways.
Cabin in Lamoine

Unique, Whimsical Off-Grid Cabin

FamilyKitchenLayout

4.97 out of 5 average rating, 304 reviews
Top guest favorite
A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.
Home in Northport

Cute Midcoast Cottage w Hot Tub

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 282 reviews
Guest favorite
Treehouse in Hancock

Acadia Treehouse near Bar Harbor - Private Luxury

Indoor spacesKitchenSleep quality

4.94 out of 5 average rating, 587 reviews
Top guest favorite
A two-story post and beam house is set on a spacious green lawn, surrounded by trees and autumn foliage. The exterior features wooden siding with multiple windows, showcasing a blend of rustic charm and natural beauty.
Home in Swans Island

Hot Tub Time Machine

FamilyKitchenOutdoor spaces

4.95 out of 5 average rating, 327 reviews
Top guest favorite
A spacious dock extends over the calm waters, surrounded by greenery. Adirondack chairs are positioned for relaxation. A potted plant adds a touch of color, with a gentle rope railing highlighting the edge. Forested hills form a serene backdrop across the lake.
Apartment in Ellsworth

Lakeside Studio with hot tub, kayaks and canoe

KitchenFamilyCondition

4.97 out of 5 average rating, 368 reviews

Family- and pet-friendly home rentals

Guest favorite
A serene outdoor space features wooden seating facing the lake, surrounded by tall trees. The grassy area leads to a pebble fire pit, creating a cozy gathering spot. The calm water reflects the clear blue sky, enhancing the natural setting.
Home in Ellsworth

Coveside Lakehouse on Sandy Point

KitchenFamilyGetting around

4.96 out of 5 average rating, 158 reviews
Top guest favorite
The log cabin stands surrounded by lush greenery, featuring a welcoming entryway with a stone pathway leading to the front door. Large windows allow natural light to illuminate the facade, while well-maintained gardens frame the inviting exterior.
Home in Verona Island

Cabin on the rocks

FamilyIndoor spacesLaundry

4.89 out of 5 average rating, 122 reviews
Top guest favorite
A serene lakeside view captures a dock extending into the water, featuring a blue paddle boat. A flag gently waves in the breeze, while vibrant red chairs are positioned on the grassy area near the shore, framed by trees and a clear blue sky.
Cottage in Otis

Cozy cottage close to Acadia National Park!

Indoor spacesKitchenHiking

4.97 out of 5 average rating, 121 reviews
Top guest favorite
Apartment in Belfast

Belfast Harbor Loft | Downtown

Indoor spacesKitchenValue

4.96 out of 5 average rating, 432 reviews
Guest favorite
A white railing and sturdy bench overlook the calm waters of Graham Lake. Tall trees frame the view, creating a serene and peaceful atmosphere. The surface of the water reflects the blue sky and surrounding greenery, offering a glimpse of the natural beauty that surrounds the property.
Cottage in Ellsworth

Lakefront, near Bar Harbor, ME

FamilyIndoor spacesValue

4.79 out of 5 average rating, 264 reviews
Top guest favorite
The log home's exterior features a large, angled window surrounded by tall trees. A wooden deck is visible, and natural stone landscaping with patches of vibrant foliage is present in the foreground, capturing the home's serene connection to the forest.
Chalet in Gouldsboro

Great Timbers Retreat Minutes from Schoodic Park

Indoor spacesFamilyQuiet

4.94 out of 5 average rating, 364 reviews
Top guest favorite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson

Lakefront Log Cabin on Pleasant Lake

Indoor spacesKitchenGetting around

4.94 out of 5 average rating, 243 reviews
Guest favorite
The open living area is highlighted by a large area rug featuring a geometric pattern. A cozy leather sofa is positioned next to a glass coffee table. Natural light filters in through multiple windows, illuminating a dining space with a wooden table and chairs.
Home in Ellsworth

The Acadia House on Westwood

KitchenIndoor spacesGrill

4.94 out of 5 average rating, 209 reviews

Family-friendly home rentals with a pool

Guest favorite
Home in Bangor

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

FamilyKitchenBackyard

4.97 out of 5 average rating, 372 reviews
Guest favorite
Home in South Thomaston

Large private area, close to Rockland

KitchenIndoor spacesPool

4.94 out of 5 average rating, 117 reviews
Guest favorite
Cabin in Orland

Camping Cabin

FamilyBreakfastLocation

5.0 out of 5 average rating, 9 reviews
Guest favorite
The house is set on a grassy hill, surrounded by neatly trimmed bushes and rocks. A welcoming porched area wraps around the front, and the roof features dormer windows. The backdrop consists of a clear blue sky with scattered clouds, creating an inviting atmosphere.
Home in Belfast

Gorgeous house with a view

KitchenIndoor spacesBackyard

5.0 out of 5 average rating, 46 reviews
Superhost
An in-ground pool is surrounded by a concrete deck, featuring a roofed area with three bar stools. Lush greenery lines the perimeter, ensuring a private and peaceful environment. The clear blue water is inviting, ideal for summer relaxation and recreation.
Home in Tremont

Large MDI house w/pool perfect for groups+families

Indoor spacesKitchenGrill

4.71 out of 5 average rating, 51 reviews
Guest favorite
Cottage in Belfast

Oceanfront Shore Cottage - Newly Renovated

FamilyKitchenOutdoor spaces

4.84 out of 5 average rating, 44 reviews
Guest favorite
Home in Bangor

New Boho Cape with Pool! Fenced yard, pet friendly

KitchenFamilyGrill

4.96 out of 5 average rating, 81 reviews
Guest favorite
A rustic cabin interior features warm wooden walls and ceiling beams. Two bunk beds and a spacious bed are arranged within the room. Natural light streams through two windows, highlighting a simple table and stool set. A wall clock adds a functional touch to the decor.
Cabin in Trenton

Camping Cabin at Wild Acadia

Indoor spacesFamilyWifi

4.97 out of 5 average rating, 35 reviews

When is the best time to visit Orland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,635 GYDG$41,635 GYDG$45,610 GYDG$41,635 GYDG$52,305 GYDG$55,234 GYDG$55,652 GYDG$55,443 GYDG$44,145 GYDG$47,074 GYDG$47,074 GYDG$42,471 GYD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Destinations to explore