
Family-friendly holiday rentals in Woolwich
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Top-rated family-friendly rentals in Woolwich
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Pet Friendly Audubon Bring Your Fishing Gear!
Enjoy the view from this wonderful 1940's waterfront cottage on the Sasanoa River in Woolwich. From here access Reid or Popham Beach State Parks with ease. Visit Maine Maritime museum in Bath, the "City of Ships." Head to Portland for a night out. Just relax and watch the seals, osprey and eagles. Rent a boat to enjoy all this extremely special waterway has to offer. Around the corner is the Kennebec River and Merrymeeting Bay, to the south you'll discover Phippsburg and historical Fort Popham.

Tiny A-Frame Romantic Getaway
Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a quarter mile off Coastal Route 1. With Historic Wiscasset, Booth Bay, Bath, Freeport, and Portland all at your fingertips, it’s the perfect romantic getaway. Spend your days exploring coastal Maine and your nights soaking in the hot tub with a glass of Malbec. Stay for a while and explore the growing restaurant scene in Wiscasset and the entire Midcoast region. See you soon!

1820s Maine Cottage with Garden
Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

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.

Waterfront Farmhouse with Modern Flair!
On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

Waterfront Sunrise Cove Cottage
Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Not recommended for those with mobility issues. Bathroom is downstairs, bedroom is upstairs. Owners live on property with small dog.

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

The Cottage
Welcome to The Cottage—your cozy getaway in the heart of Bath, Maine! Perfectly situated near charming coastal towns, beautiful beaches, and scenic hiking trails, this retreat offers a comfy living area, fully equipped kitchen, and four inviting bedrooms. Sip your morning coffee from the sunny dining room window seat, or wind down by the fire pit out front. Note: The Cottage is attached to the owner’s home, but you’ll have full privacy throughout your stay.

Retreat at Sea Cloud Cottage in Historic Wiscasset
Welcome to Sea Cloud Cottage - A Charming Retreat in Wiscasset, Maine Sea Cloud Cottage is a beautiful one-bedroom home, once the guest house to the larger Acorn Cottage next door. Perfectly designed for a couple or small family (with an extra child or adult on the pull-out sofa), this 900-square-foot gem offers an inviting, comfortable space for your getaway. You can also rent it alongside Acorn Cottage for larger parties, accommodating up to 9 guests.

Private Guest Apartment with separate entrance.
Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking. sitting room with a dining table that looks out onto the deck, queen bedroom, private bathroom with jetted tub and separate shower, fully equipped kitchenette; NEW FURNACE-quiet and efficient.

Spectacular River Retreat with Hiking Trails
Spectacular listing brought to you by seasoned Bath Superhosts! Enjoy sweeping views of the Kennebec River while cozying up by the fireplace. This modern art filled minimalist house sits on a bluff overlooking the Kennebec River and leads into Bath's peaceful Thorne Head Preserve, a vast network of trails that climb and hug the river's edge. It's just minutes away from downtown Bath, the historic and charming City of Ships.

Modern 1-BR I Wooded Retreat I Mid-Coast Maine
Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!
Popular amenities for Woolwich family-friendly rentals
Family-friendly home rentals with a hot tub

Treehouse With Hot Tub Close to Sunday River!

Tiny house in the Birch Grove with private HOT TUB

Hallowell Hilltop Home with Hot Tub & Sauna

LUX Designer Private Waterfront Hot Tub - Secluded

Downtown Hideaway-Loft HotTub Modern Clean Private

A comforting sweet off grid cabin near the beach!

Cozy log cabin on private pond, near Reid St Park!

Cozy Rock Cabin #thewaylifeshouldbe
Family- and pet-friendly home rentals

Joyful Maine Escape: 3 Bdr. Waterview Townhouse

Studio Apartment in Freeport

Loon Lodge

Maplenook Tiny Cabin - A Cozy Woodland Oasis

Cottage on Todd Bay

The Byre at Piper’s Pond

Rustic Farmhouse at Oxbow Brewery

Linekin Guest Suite
Family-friendly home rentals with a pool

Cozy Studio Flat, Belgrade Lakes Region

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

Luxe Liberty: Getaway with Heated Indoor Pool!

Portland Sweet Escape

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Poolside Suite-Gateway to Portland

Loft Apartment on Tree-Lined Street in Falmouth

Maine Hacienda w/hot tub & seasonal pool
When is the best time to visit Woolwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $226 SGD | $233 SGD | $233 SGD | $237 SGD | $309 SGD | $326 SGD | $397 SGD | $409 SGD | $351 SGD | $291 SGD | $300 SGD | $208 SGD |
| 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 |
Quick stats about holiday rentals that are family-friendly in Woolwich

Total holiday rentals
Explore 40 holiday rentals in Woolwich

Nightly prices starting at
Woolwich holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 2,150 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Woolwich holiday rentals include wifi access

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

4.9 Average rating
Woolwich stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Sagadahoc County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Scarborough Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- East End Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Palace Playland
- The Camden Snow Bowl
- Hills Beach
- Maine Maritime Museum
- Portland Museum of Art
- Farnsworth Art Museum
- Bradbury Mountain State Park
- Fortunes Rocks Beach
- Rockland Breakwater Light
- Aquaboggan Water Park
- Bug Light Park
- Pineland Farms




