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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$27,197 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 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.

Indoor spacesFamilyLaundry

4.98 out of 5 average rating, 127 reviews
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!

KitchenFamilyWifi

4.98 out of 5 average rating, 209 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

Indoor spacesKitchenTV

5.0 out of 5 average rating, 163 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!!!

Indoor spacesFamilyHiking

5.0 out of 5 average rating, 147 reviews
Top guest favorite
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.

Indoor spacesKitchenComfort

4.93 out of 5 average rating, 161 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.

Indoor spacesFamilyGrill

4.97 out of 5 average rating, 135 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 spacesWalkability

4.97 out of 5 average rating, 151 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.

KitchenFamilyBreakfast

4.94 out of 5 average rating, 179 reviews
Top guest favorite
Cottage in Ellsworth

Gateway Cottage Acadia Natl Park Bar Harbor

Keep life simple at this TINY, cozy, peaceful "cottage in the woods" with little surprises and big charm around every corner. Centrally-located to many attractions such as Acadia National Park, Bar Harbor, Whale Watching and tours. Less than 5 minutes from local Ellsworth restaurants, shops, gas stations and supermarkets. The sunroom is perfect for morning coffee, winding down with a glass of wine or curling up with a good book on the boat bed.

FamilyKitchenLaundry

4.99 out of 5 average rating, 147 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.

FamilyKitchenCondition

4.99 out of 5 average rating, 155 reviews
Top guest favorite
A serene lakeside scene captures the sunset over Toddy Pond, with vibrant shades of orange and purple reflecting off the calm water's surface. Silhouettes of trees outline the horizon, while mist gently rises above the lake, enhancing the tranquil atmosphere.
Campsite in Penobscot

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.

KitchenIndoor spacesQuiet

4.99 out of 5 average rating, 143 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

Indoor spacesFamilyLong stay

4.95 out of 5 average rating, 913 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 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

FamilyKitchenPool

4.97 out of 5 average rating, 188 reviews
Superhost
Home in Penobscot

Delight<Farmhouse

KitchenIndoor spacesWifi

4.91 out of 5 average rating, 127 reviews
Superhost
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

FamilyKitchenNearby

4.9 out of 5 average rating, 272 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

FamilyKitchenLocation

4.95 out of 5 average rating, 106 reviews
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!

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 307 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 spacesFamilyWifi

4.98 out of 5 average rating, 274 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

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 295 reviews
Top guest favorite
Home in Brewer

Riverside Getaway w/HotTub | 3br 2 bth

KitchenIndoor spacesCheckout

4.86 out of 5 average rating, 126 reviews

Family- and pet-friendly home rentals

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

KitchenFamilyWifi

4.89 out of 5 average rating, 120 reviews
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

KitchenIndoor spacesGrill

4.96 out of 5 average rating, 153 reviews
Top guest favorite
Home in Stockton Springs

Private Beach, Bar Harbor, Acadia, 15 beds, Pets

Indoor spacesKitchenCondition

4.91 out of 5 average rating, 111 reviews
Guest favorite
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 spacesBeach

4.96 out of 5 average rating, 146 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

Branch Lake Cabin minutes to Acadia (Weekend deal)

KitchenFamilyParking

4.88 out of 5 average rating, 112 reviews
Top guest favorite
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

KitchenIndoor spacesWifi

4.98 out of 5 average rating, 179 reviews
Top guest favorite
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

FamilyIndoor spacesWalkability

4.99 out of 5 average rating, 145 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!

FamilyIndoor spacesBackyard

4.97 out of 5 average rating, 120 reviews

Family-friendly home rentals with a pool

Guest favorite
Home in Bangor

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

Indoor spacesFamilyComfort

4.97 out of 5 average rating, 369 reviews
Guest favorite
Home in South Thomaston

Large private area, close to Rockland

FamilyIndoor spacesLocation

4.94 out of 5 average rating, 113 reviews
Guest favorite
Cabin in Orland

Camping Cabin

FamilyAccuracyNearby

5.0 out of 5 average rating, 7 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 spacesKitchenQuiet

5.0 out of 5 average rating, 30 reviews
Top 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

FamilyKitchenPool

5.0 out of 5 average rating, 44 reviews
Guest favorite
The backyard features a fenced-in in-ground pool, surrounded by a concrete patio. Colorful floatables and pool toys are scattered throughout the clear water. Several lounge chairs are positioned poolside, providing space for relaxation in a tranquil outdoor setting.
Home in Bangor

New Boho Cape with Pool! Fenced yard, pet friendly

Indoor spacesKitchenCheckout

4.96 out of 5 average rating, 75 reviews
Guest favorite
Cottage in Belfast

Oceanfront Shore Cottage - Newly Renovated

Indoor spacesFamilyAccuracy

4.84 out of 5 average rating, 43 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 spacesFamilyBathroom

4.71 out of 5 average rating, 51 reviews

When is the best time to visit Orland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,632 GYDG$41,632 GYDG$45,606 GYDG$41,632 GYDG$52,301 GYDG$55,230 GYDG$55,648 GYDG$55,439 GYDG$44,142 GYDG$47,071 GYDG$47,071 GYDG$42,468 GYD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Destinations to explore