Family-friendly vacation rentals in Orland

4.98 out of 5 average rating, 211 reviews

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!

KitchenIndoor spacesSleep quality

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.

4.98 out of 5 average rating, 127 reviews

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.

Indoor spacesFamilyLaundry

5.0 out of 5 average rating, 167 reviews

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

FamilyIndoor spacesHiking

5.0 out of 5 average rating, 149 reviews

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!!!

KitchenFamilyParking

4.93 out of 5 average rating, 163 reviews

The charming exterior of a cottage is highlighted by blue wood siding and yellow trim. A flower bed with colorful blooms lines the gravel path leading to the entrance. A decorative birdhouse rests on a tree nearby, complementing the natural surroundings.

Cottage in Surry

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.

FamilyIndoor spacesOutdoor spaces

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.

4.97 out of 5 average rating, 140 reviews

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.

Indoor spacesFamilyShared spaces

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.

4.97 out of 5 average rating, 152 reviews

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 spacesDecor

4.97 out of 5 average rating, 190 reviews

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.

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 156 reviews

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 spacesOutdoor spaces

4.94 out of 5 average rating, 918 reviews

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

FamilyKitchenHospitality

4.99 out of 5 average rating, 138 reviews

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 spacesFamilyNearby

The exterior of a two-story house is set against a clear blue sky and surrounded by trees. A spacious lawn features a fire pit with several Adirondack chairs arranged around it, inviting gatherings. The driveway provides access to the house, enhancing its private setting.

4.96 out of 5 average rating, 116 reviews

Tides' Reach - Private Waterfront King Beds

Twenty-five private acres. Six hundred feet of waterfront. Zero neighbors. Watch the tides from the gourmet kitchen, roast s'mores at the fire pit, explore down to the shore. Bucksport 5 min, Acadia 1 hr, Bangor airport 40 min. Well-behaved dogs welcome

KitchenIndoor spacesRiver

Popular amenities for Orland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Place to stay in Owls Head

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.

4.98 out of 5 average rating, 309 reviews

A comforting sweet off grid cabin near the beach!

FamilyIndoor spacesView

4.91 out of 5 average rating, 129 reviews

Home in Penobscot

Delight<Farmhouse

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 107 reviews

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

FamilyKitchenNearby

4.98 out of 5 average rating, 278 reviews

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

KitchenFamilySleep quality

4.91 out of 5 average rating, 276 reviews

A spacious white tipi is nestled among trees, with a clear view of a quiet lake. A picnic table sits nearby, accompanied by a hammock stretched between two trees, inviting relaxation in this serene natural setting.

Tent in Brooks

Waterfront Tipi Glamping // Phoenix Landing

Indoor spacesKitchenAccess

4.97 out of 5 average rating, 300 reviews

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

FamilyKitchenQuiet

4.95 out of 5 average rating, 324 reviews

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

KitchenIndoor spacesPool

4.97 out of 5 average rating, 367 reviews

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

KitchenFamilyHot tub

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 150 reviews

An interior view of the yurt features a full bed with floral bedding, a comfortable green sofa, and a patterned area rug. A wood stove is positioned centrally, with logs stacked nearby. Ambient lighting is provided by string lights along the interior walls.

Yurt in Dedham

Farm stay in a cozy yurt

FamilyIndoor spacesView

4.98 out of 5 average rating, 181 reviews

The cabin exterior is softly illuminated by string lights, enhancing the porch area. A cozy seating arrangement is visible, complemented by a wooden railing and steps leading to the yard. Surrounding trees provide a natural backdrop under the twilight sky.

Cottage in Bucksport

Cozy Cottage in the Woods

FamilyKitchenCleanliness

4.94 out of 5 average rating, 180 reviews

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

FamilyKitchenBathroom

4.97 out of 5 average rating, 120 reviews

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 spacesFamilyGrill

4.96 out of 5 average rating, 156 reviews

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

FamilyKitchenOutdoor spaces

4.88 out of 5 average rating, 113 reviews

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

Branch Lake Cabin minutes to Acadia (Weekend deal)

KitchenIndoor spacesHiking

4.99 out of 5 average rating, 146 reviews

The charming exterior of a Cape Cod-style cottage is displayed, featuring gray siding and white window trims. A red door is centered between two bay windows adorned with planters. An American flag is proudly displayed, and seasonal decorations, including pumpkins, enhance the welcoming entrance.

Home in Verona Island

The Ward House

KitchenIndoor spacesBathroom

4.79 out of 5 average rating, 264 reviews

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

FamilyKitchenComfort

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 372 reviews

Home in Bangor

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

FamilyKitchenQuiet

4.94 out of 5 average rating, 116 reviews

Home in South Thomaston

Large private area, close to Rockland

KitchenFamilyComfort

5.0 out of 5 average rating, 9 reviews

Cabin in Orland

Camping Cabin

FamilyOutdoor spacesCleanliness

4.99 out of 5 average rating, 94 reviews

An expansive outdoor area features a private pool surrounded by a brick patio. Comfortable seating is arranged nearby under a clear blue sky, showcasing the elegant architecture of the mansion in the background, set against lush greenery.

Home in Ellsworth

The Jarvis Homestead | Historic Maine Mansion

KitchenFamilyComfort

4.97 out of 5 average rating, 32 reviews

A wooden interior space is highlighted by a pitched ceiling lined with warm wooden panels. A dining table is set for four, while a fully equipped kitchen features modern appliances. Barstools are positioned at a counter, and a staircase leads to an upper loft area.

Cabin in Trenton

Deluxe Cabin C at Wild Acadia

FamilyIndoor spacesHospitality

5.0 out of 5 average rating, 46 reviews

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

KitchenFamilyQuiet