
Family-friendly holiday rentals in Waldoboro
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Waldoboro

Total holiday rentals
Explore 50 holiday rentals in Waldoboro

Nightly prices starting at
Waldoboro holiday rentals start at $135 NZD per night before taxes and fees

Verified guest reviews
Over 1,780 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Waldoboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Waldoboro rentals

4.9 Average rating
Waldoboro stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Waldoboro
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Country home ~ Family friendly
Our converted barn is located on a little used road with easy access to miles of trails. Our road is little used but intersects with US 1.There is a downstairs bedroom with an open loft on the second floor. Wonderful light and views. A fire-pit, swings, hammocks, and playground structures make this a perfect place to stay with your family. A peaceful place to visit for all ages. World famous Moody's diner, a grocery store and gas stations etc. are just 3 miles away! Perfect for young children.
KitchenFamilyGetting around

‘Round the Bend Farm - private, modern cabin
Our newly built, modern cabin offers a secluded and relaxing retreat in Union, Maine. With the high ceilings, open floor plan, and many windows, guests are surrounded by natural light and forest views. The cabin has a fully equipped kitchen, a cozy fireplace, and an outdoor grill and fire pit. Walking trails connect the cabin to our farm next door, where you can visit with our horses, donkeys, goats, chickens, and ducks. We are just 25 minutes from the Midcoast's shops, restaurants, and beaches.
KitchenIndoor spacesBreakfast

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.
Indoor spacesFamilyGetting around

Downtown-Walk to All Things Rockland
Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!
FamilyIndoor spacesBathroom

The Apple Blossom Cottage
The Apple Blossom is located in the heart of historic Union village,in Sky Orchard. It is nestled down the hill in a private orchard.The tiniest of tiny houses.Two minutes to pizza,The Sterlingtown Public House,coffee shop,and grocery.15 minutes from the ocean!Sit on the deck and watch the fireflies in the field.With a fireplace and view of the blueberry hills.Curl up, listen to the rain on the tin roof,awaken to the sunrise through the antique lace curtains.This place will fill your soul.
FamilyKitchenOutdoor spaces

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!
Indoor spacesKitchenRiver

Finding Joy
This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.
Indoor spacesKitchenBiking

Crow’s Nest Tiny House at Old Crow Ranch
The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.
KitchenIndoor spacesNearby

The Copper Fox Treehouse
Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse
KitchenFamilyLayout

Private tree-top loft 5 minutes from Damariscotta.
Relax in this cozy loft with a light-filled deck overlooking the woods, but just five minutes to downtown Damariscotta. This brand new loft above our barn is cozy with all you need for a perfect vacation. You can relax with your morning coffee above the trees. It has an indoor toilet, sink and breakfast bar and outdoor shower. We’re a semi-retired couple and love to share our 62 acres property with stream and meadow. There are quite a few stairs to the loft.
FamilyKitchenQuiet

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.
KitchenIndoor spacesCleanliness

1830s Cape hosted by George & Paul
This 1830 cape is for rent by the month or weekly or for a two-night minimum stay. It is located at the edge of the historic village of Waldoboro. It offers a convenient base to sightseeing in midcoast Maine. It’s old-fashioned, decorated with plants, antiques and paintings and features a large, fully equipped kitchen, music room with piano, television room with pull-out sofa, full bath with stall shower and outside patio. Your hosts are right across the driveway.
Indoor spacesFamilyComfort
Popular amenities for Waldoboro family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy romantic A-frame by a woodland stream - 25
FamilyIndoor spacesHeating

Maybelle the Tiny Cabin on 100 acres
FamilyIndoor spacesAccess

Tiny house in the Birch Grove with private HOT TUB
KitchenIndoor spacesLayout

Beachfront Guest Cottage - Year-round Hot Tub!
KitchenIndoor spacesSleep quality

Cute Midcoast Cottage w Hot Tub
Indoor spacesKitchenLaundry

Modern Treehouse w/Water Views+Cedar Hot Tub
FamilyKitchenHiking

Birch Hill Cabin w/Hot Tub
Indoor spacesFamilyHospitality

Raven's Crossing - Retreat Cottage
KitchenFamilySleep quality
Family- and pet-friendly home rentals

Timeless Tides Cottage
Indoor spacesFamilyRiver

Loon Lodge
KitchenFamilyBathroom

Maine Waterfront Hideaway
FamilyIndoor spacesCondition

Stunning Mountain & Ocean Post&Beam
Indoor spacesFamilyNearby

Little Apple Cabin on 5 acres, amazing stargazing!
KitchenFamilyDecor

Simple Boothbay Log Cabin on Water
Indoor spacesKitchenOutdoor spaces

Peaceful & private waterfront cabin
KitchenIndoor spacesTV

Cozy Carriage House in Downtown Damariscotta
KitchenFamilyPets
Family-friendly home rentals with a pool

Resort-like 2 bed/1 bath - seasonal pool/hot tub
Indoor spacesFamilyOutdoor spaces

A Riot of Color at an Artist's Retreat on the Port
Indoor spacesFamilyParks

House in the woods
KitchenIndoor spacesCleanliness

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
FamilyIndoor spacesAccuracy

Luxury Retreat In Back Cove | 10 Min to Downtown
Indoor spacesFamilyHospitality

Loft Apartment on Tree-Lined Street in Falmouth
KitchenFamilyParks

OOB Oasis: 6BR Home w/ Private Pool Near Beach
KitchenFamilyCleanliness

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
KitchenIndoor spacesRiver
When is the best time to visit Waldoboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $410 NZD | $447 NZD | $474 NZD | $430 NZD | $518 NZD | $464 NZD | $479 NZD | $505 NZD | $417 NZD | $430 NZD | $469 NZD | $423 NZD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Destinations to explore
- Popham Beach, Phippsburg
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Sand Beach
- Bradbury Mountain State Park
- Reid State Park
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Pineland Farms
- Belgrade Lakes Golf Club
- Range Ponds State Park
- Lost Valley Ski Area





