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Family-friendly holiday rentals in Orland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Orland family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cabin in Appleton
4.89 out of 5 average rating, 307 reviews

Raven's Crossing - Kate's Cottage

KendraRating, 5 stars2 weeks ago
A beautiful rustic cabin in an amazing spot. Lori is a great host and is always near in her farmhouse to communicate and get you what you need. Appleton is not far from Camden / Rockland but has that rustic getaway feel. The option of adding a wonderful soak in the hot tub, wood fired sauna, massage and breakfast are available as well. I’ll be back next year! Thank you for everything, Lori!
Farm stay in Searsport
4.91 out of 5 average rating, 112 reviews

Latham Blueberry Farm for up to 6 guests.

AshleyRating, 5 stars10 months ago
We couldn’t have asked for a better stay at Latham blueberry farm. Doug and Brenda were incredibly helpful and friendly- they introduced us to the house and farm as soon as we checked in and were always available if needed. The beds were comfy, the kitchenette stocked, and the grounds were gorgeous. Their beautiful 1826 farm house was an authentic experience of staying on a farm- our kids loved feeding the animals (especially Ernie the pig and Moses the horse); picking fresh blueberries; and swimming and paddleboating in the private pond. Our hosts had great recommendations for local outings, and we loved chatting with them and playing with their puppy Jackie. Our family made lifetime memories.
Top guest favourite
Home in Holden
4.96 out of 5 average rating, 245 reviews

Chalet Central

IoanaRating, 5 stars2 weeks ago
We loved our time at Dwayne and Patti’s place! It definitely felt like a home rather than a hotel, which is exactly what we want when we book an Airbnb over a hotel. The musical instruments and hot tub were a hit with our group :) The location is amazing, close to both Bar Harbor (Acadia) and Bangor. We got to go to a concert and hiking during our stay, and we loved returning to our home base. I can’t want to be back!!
Guest favourite
Loft in Lincolnville
4.96 out of 5 average rating, 47 reviews

Oceanfront Loft with gorgeous water views & beach!

JenniferRating, 5 stars2 weeks ago
This place is so lovely and peaceful. We loved the water view from the loft and roaming the beach. It is a great spot.
Guest favourite
Guest house in Appleton
4.9 out of 5 average rating, 298 reviews

Raven's Crossing - Retreat Cottage

AylaRating, 5 stars2 months ago
What an awesome place to stay! Lori was incredibly gracious and accommodating with out late arrival. The cabin towards the back of the property was so cozy. Fantastic stay and would definitely recommend!
Home in Rockland
4.92 out of 5 average rating, 50 reviews

Relaxed South End Bungalow-5 mins to downtown

BillieRating, 5 stars56 months ago
Just the right size, a home away from home. Clean, neat, cozy, and quaint. Alyssa has been a great host from beginning to the end. Very quick response time. The home is in a perfect location. Would definitely stay again.
Superhost
Home in Lincolnville
4.92 out of 5 average rating, 13 reviews

Gorgeous Home w/fantastic views -10 mins to Camden

SusanRating, 5 stars10 months ago
Beautiful home with a great view, deer and turkeys in the front yard. Very quiet and peaceful. The home is well equipped and spacious.
Guest favourite
Home in Surry
4.89 out of 5 average rating, 228 reviews

Peaceful retreat on Newbury Neck

TaylorRating, 5 stars1 week ago
The home was spotless and comfortable. Back patio was cozy and we really enjoyed relaxing in the private hot tub while listening to the owls. The entire process was seamless and easy! We will definitely be back.

Family- and pet-friendly home rentals

Guest favourite
Cabin in Hancock
4.95 out of 5 average rating, 149 reviews

Blackberry Cottage at Crabtree Neck Cottages

WestahRating, 5 stars2 weeks ago
Blackberry Cottage is so cozy and quaint. Suzanne is a fantastic hostess and is quick to respond if needed. The cabin is on property with other cabins, but this one feels secluded so you feel you are in a private location. The cabin was clean and the kitchen had all of the amenities we needed for our stay. We stopped and picked up groceries on the way in so we could cooks a few meals during our stay. The only suggestion I would make is to provide some sort of solid covering for the bathroom window apart from the lace curtain. There are woods next to the bathroom, but it would be more comfortable when showering at night if we had the option to cover the window with a shade or solid curtain.
Superhost
Guest house in Blue Hill
4.73 out of 5 average rating, 150 reviews

Bungalhigh with Swimming Cove

JillRating, 5 stars8 months ago
This was such a delightful, peaceful & beautiful place to stay. Shelby was extremely responsive & helpful. I appreciated that she went the extra mile to alert me to the Aurora Borealis & encourage me to see it from the point. When the power went out b/c of a local car accident, she kept me updated with information about cause & when power was expected to return & provided flashlights & a special battery powered lightbulb to provide light. I couldn't have asked for more!
Top guest favourite
Cottage in Ellsworth
4.88 out of 5 average rating, 102 reviews

Peaceful Branch Lake Cabin minutes to Acadia

ChristopherRating, 5 stars2 weeks ago
The cabin was breathtaking, with a history painted and photographed among her walls. Perfect amount of space to accommodate a family should you have one. The morning sunrise was spiritual, and humbling. Host was incredibly friendly and accommodating for our dog. Arjuna. Will absolutely be returning. Thank you for an amazing and beautiful experience.
Superhost
Cottage in Ellsworth
4.87 out of 5 average rating, 288 reviews

Modern cottage with hummingbirds

JulieRating, 5 stars3 days ago
We liked the privacy and seclusion of the house, as well as, having good wifi and space for our dog. The windows around the house let in so much light and we could see wild turkeys in the field one night. The house is close enough to what Acadia, Ellsworth, and Bar Harbor has to offer, but is away from the congestion. Having a washer/ dryer is a plus. We had a great stay of 5 days.
Guest favourite
Cabin in Deer Isle
4.88 out of 5 average rating, 144 reviews

Long Cove Artist Cottage

Carmen Rating, 5 stars2 weeks ago
My husband and I spent a wonderful week at Judith’s cottage in Deer Isle. Judith, her partner Linda, and Kate (Linda's daughter) were incredibly welcoming—always kind, helpful, and full of great recommendations about the area, from hiking trails and restaurants to local shops and the island’s fascinating history. We truly enjoyed our conversations with them, and they were also very respectful of our privacy. The cottage is rustic but cozy and comfortable, with everything we needed for a relaxing stay. The Wi-Fi worked well, and the garden and views of the cove were beautiful. It’s also a great location for exploring Deer Isle, the Blue Hill Peninsula, and even Acadia National Park. We’re grateful for the hospitality and would gladly return!
Superhost
Home in Bar Harbor
4.85 out of 5 average rating, 178 reviews

Abby Lane

MehulRating, 5 stars10 months ago
Aaron's place was fantastic for our party of 6 (my partner and me, our kids, her parents). The house was located perfectly on the North end of Mt. Desert Island by Hadley Point Beach (where we were lucky to catch both a meteor shower and the Northern Lights.) While the lower level had a separate entrance, the kids appreciated the additional privacy/area away from adults. The entire house was clean and the beds were very comfortable. All of the amenities (well stocked kitchen, two bathrooms, washer/dryer, patio) were much appreciated. We'd definitely stay again when visiting Acadia.
Guest favourite
Home in Newcastle
4.91 out of 5 average rating, 201 reviews

Rustic Farmhouse at Oxbow Brewery

CatherineRating, 5 stars3 weeks ago
My husband and in-laws and I and our two dogs stayed for a long MDW. The weather did not cooperate but did not hinder us. Especially staying at this Airbnb on the beautiful Oxbow Brewing property. In fact the coziness of the space made a rainy day even more fun. We were visiting for the racetrack and location was excellent for privacy and also close to local attractions. Wish we had more of a group to experience the space with us, it was really special!
Guest favourite
Home in Stetson
4.95 out of 5 average rating, 197 reviews

Lakefront Log Cabin on Pleasant Lake

LoraRating, 5 stars3 weeks ago
The lakeside cabin was just what I needed. Quiet, private, and right on the water. My dog loved running in the yard and swimming in the lake. The cabin was comfortable with all the basics, and sitting on the porch watching the water was so relaxing. Perfect spot to unwind and enjoy some peace and quiet.

Family-friendly home rentals with a pool

Top guest favourite
Flat in Boothbay Harbor
5 out of 5 average rating, 32 reviews

Luxury Condo on Water's Edge in Boothbay Harbor

HollyRating, 5 stars2 months ago
A few times while wandering around midcoast Maine in late March, we were asked if this is when we usually came to vacation here. Yes, we are educators from the Southwest, and this was our spring break, so this is when we came to visit, but honestly, it is so peaceful this time of year. Especially Boothbay Harbor, and what we imagined while walking around the very quiet town would be a very different place in July! Our experience at Abby’s space was absolutely wonderful and serene in the spring. The thoughtful touches (thank you for the bottle of Maine wine and jar of blueberry jelly!) made it even more special. Thank you, we hope to be back one day.
Superhost
Home in Stonington

Kate's House at Spruce Harbor

ShokiRating, 5 stars9 months ago
Cannot imagine a better spot to relax with our family. A lucky spot for the owners and luckier for us that they share the rental with strangers.
Superhost
Flat in Rockland

Heart of Rockland Maine

DeborahRating, 5 stars8 months ago
Aimee was wonderful to deal with. Her place was absolutely beautiful. we definitely picked the right place. the sunrises were so awesome. Rockland was a gorgeous little town.
Apartment in Rockport

Samoset Resort Oceanfront Large One Bedroom

JamesRating, 5 stars72 months ago
Great unit on the golf. Course with Ocean views out to the islands. Generally peaceful, save for the morning mowing of the golf course. Great place to base to see all of the mid-coast and the Samoset hotel amenities that are available to you are first class
Apartment in Rockport

Samoset Resort Oceanfront Condominium

ArleneRating, 5 stars84 months ago
This place is absolutely amazing. It was larger than expected. It looked smaller in the pictures. Everything in the apartment was squeaky clean and we had every single thing we needed, from pots and pans to board games. Great ocean view from the porch, the living room and from one of the bedrooms. I loved seeing the boats pass by. So peaceful! I stayed there with my elderly mom, my teenage daughter and her friend for 4 days. There was so much to do! We enjoyed both the outdoor and the indoor pool. The kids took advantage of the Health Club by playing ping pong, badminton and going to the video game room. They also spent several hours playing chess in a very nice room near the lounge area that had a gorgeous ocean view. We had dinner at the Italian restaurant in the resort and were impressed by the amazing view. Great service. We also enjoyed the long walk to the lighthouse right next to the resort, and loved going to Camden, such a charming little town, 10 minutes away. The hostess, Laurie, was very accommodating, super nice, and communicated with me frequently, making sure I had all the answers I needed. I would definitely go back there! Glad to have made such wonderful memories! We didn't want to leave!
Home in Lamoine

Close to Acadia National Park

EdmundRating, 5 stars34 months ago
Valerie's home was clean and in a quiet neighborhood peaceful stay
Guest favourite
Flat in Stonington
4.93 out of 5 average rating, 15 reviews

The Carriage House at Spruce Harbor

TimRating, 5 stars10 months ago
My husband and I, and our two pups had a fantastic time in the Carriage House for a week. Part of a breathtaking private/secret compound on the water…with the most incredible private tidal pool. The place is so authentic, which is what we love about staying in ME when we can escape. We were so blessed to find Margaret’s place last minute. Margaret’s mother, Sally, and her husband were in the main Kate’s house. So so sweet they were to us and our girls. A dog paradise. We are foodies. Plenty of good restaurants around - just a few minutes to the adorable village of Stonington. Around the corner is one of the best restaurants in the country - Aragosta. We can’t wait to return…hopefully, in the Fall. A trip we will always remember. Thank you, Margaret & Family.
Guest favourite
Home in South Thomaston
4.96 out of 5 average rating, 93 reviews

Large private area, close to Rockland

RachelRating, 5 stars9 months ago
We found the home clean and welcoming. There was plenty of room for all of us and we enjoyed the back deck very much. The kitchen was well equipped and although we did not do any cooking, if we had, everything was there for us. We really liked how private the home was. Had the weather been warmer we definitely would have checked out the pool. It is also very close to Thomaston, Rockland and Owls Head. So much to do in this area. We would recommend this home to anyone who wants a quiet retreat in Maine that is close to the coast.

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

  • Total rentals

    80 properties

  • Nightly prices starting at

    ₹7,754 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Hancock County
  5. Orland
  6. Family-friendly rentals