
Family-friendly vacation rentals in Orland
Find and book unique family-friendly homes on Airbnb
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$27,200 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.

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.
FamilyIndoor spacesCondition

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 spacesFamilyWalkability

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
KitchenFamilyGetting around

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!!!
KitchenIndoor spacesComfort

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 spacesKitchenCheck-in

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.
FamilyKitchenView

The Cabins at Currier Landing Cabin 2: Meadow
Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. The Cabins at Currier Landing, featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest,” are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of the Benjamin River Harbor shore. 2 seasonal cabins; 1 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.
FamilyIndoor spacesHiking

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.
KitchenFamilyLaundry

Farm stay in a cozy yurt
Want to be surrounded by nature? Listen to animal sounds? Eat quality food? You're in the right place! The yurt has a full bed. It has electricity for lights and a hot plate. Pots, pans and utensils are available. The compost toilets are in the back. There is no running water inside but we provide a drinking fountain and foot pump sink. An outdoor shower is available near our house. The distance between parking and the yurt is about 150 yards. Petting goats or sheep available. .
FamilyIndoor spacesAmenities

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.
FamilyIndoor spacesTV

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 spacesCheck-in

Field of Dreams Tiny Home
Escape to our charming tiny home near Bangor, a perfect retreat for 2. Enjoy serene field views from a panoramic window, a private hot tub, and a cozy fire pit. Inside, a modern wood-paneled interior with a projector screen for movie nights awaits. This unique stay offers tranquility and modern comfort, just minutes from the city.
Indoor spacesKitchenBathroom
Popular amenities for Orland family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Cabin in the Pines • Hot Tub + Near Acadia
KitchenFamilyAccuracy

Waterfront Tipi Glamping // Phoenix Landing
KitchenIndoor spacesBeach

Acadia Pines Cabin w/HotTub 10min2Downtown
Indoor spacesFamilyLayout

A comforting sweet off grid cabin near the beach!
Indoor spacesFamilyLong stay

SILVER MOON, a Yurt for All Seasons
FamilyIndoor spacesPets

Cute Midcoast Cottage w Hot Tub
KitchenFamilyBeach

Acadia Treehouse near Bar Harbor - Private Luxury
Indoor spacesKitchenCheckout

Unique, Whimsical Off-Grid Cabin
FamilyKitchenOutdoor spaces
Family- and pet-friendly home rentals

Waterfront Retreat | Dock, Kayaks & Outdoor Movies
Indoor spacesKitchenLong stay

Cozy Cottage in the Woods
FamilyKitchenQuiet

Coveside Lakehouse on Sandy Point
KitchenIndoor spacesParks

Gran Den Lakefront Home Near Acadia
KitchenFamilyCheckout

Cozy Cabin 3 • Forest Escape • Cedar Sauna+Firepit
KitchenIndoor spacesPool

The Sunset Chalet | PERFECT Location!
KitchenIndoor spacesSleep quality

Modern cottage with hummingbirds
FamilyIndoor spacesCondition

Quiet cottage on the bay
FamilyIndoor spacesLocation
Family-friendly home rentals with a pool

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

Large private area, close to Rockland
Indoor spacesKitchenGetting around

Camping Cabin
FamilyAccuracyHospitality

Camping Cabin at Wild Acadia
Indoor spacesKitchenHospitality

Indoor Pool*Hot Tub*Sauna*Game Room*Near Acadia
FamilyKitchenSleep quality

Ocean View Lawn Cottage - Newly Renovated 2024
Indoor spacesKitchenGetting around

Gorgeous house with a view
Indoor spacesFamilyQuiet

Bar Harbor, near Acadia with seasonal dock & pool
Indoor spacesPoolLocation
When is the best time to visit Orland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,637 GYD | G$41,637 GYD | G$45,613 GYD | G$41,637 GYD | G$52,308 GYD | G$55,238 GYD | G$55,656 GYD | G$55,447 GYD | G$44,148 GYD | G$47,077 GYD | G$47,077 GYD | G$42,474 GYD |
| 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 |
Destinations to explore
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Portland Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Bar Harbor Vacation rentals
- Salem Vacation rentals
- Halifax Vacation rentals
- York County Vacation rentals
- Cambridge Vacation rentals
- Old Orchard Beach Vacation rentals
- Acadia National Park
- Acadia National Park Pond
- Schoodic Peninsula
- The Camden Snow Bowl
- University of Maine
- Rockland Breakwater Light
- Sand Beach
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Bass Harbor Head Light Station
- Hollywood Slots Hotel & Raceway
- Echo Lake Beach





