Family-friendly vacation rentals in Wiscasset

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!

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.

25 Middle: Two floor loft w. water view -sleeps 5

A private apartment on the second and third floor of an historic house located in the heart of Wiscasset village. Featuring a bird’s eye views of the harbor and surrounded by lovely gardens.Stroll to restaurants, waterfront, antique shops, historic homes & gardens. Ideal base for touring Maine attractions. Full kitchen, five other rooms including two full baths.A//C in bedroom suite and 3rd floor loft space.Central yet private. Tastefully decorated .Not suitable for children younger than 12.

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Waterscape Cottage - private waterfront

This is where you want to stay! Away from all the traffic and noise of HWY 1, down a long driveway but super close to the village. Perched on the hillside with elevated panoramic views of the river and Wiscasset Harbor. This adorable little building is post and beam construction - comfy, quiet, peaceful on 34 acres of woodlands and river front. Want to squeeze in more kids? Talk to us. 2 quiet nonaggressive furry friends welcome. $20 per nt. per pet paid on arrival. Max pet fee $100.

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Historic Elegance at The Sunken Garden Stay

Situated in "The Prettiest Village in Maine," The Sunken Garden Stay is a stunning apartment that overlooks the historic Sunken Garden landmark. This 1784 Colonial home is beautifully presented, offering a lovely balance of open plan living and cozy, comforting space, capturing the essence of a significant time period in history. For your comfort, it has all the modern amenities of today, providing a blend of old-world charm and modern convenience.

Coastal Cotton Cottage on Sheepscot Harbour

Coastal Cotton Cottage is on beautiful Davis Island in a peaceful setting by the sea. Open the French doors from the living room and step out onto the spacious front porch to watch the sun set across Wiscasset Harbor. This cottage features two bedrooms downstairs and one single bed in the loft. NEW UPDATES THIS SPRING! Our cottage has been recently updated with fresh paint, new towels and new coastal interior decor.

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. Owners live on property with small dog.

Victorian Charm in Wiscasset, Maine: Acorn Cottage

A TRULY NOSTALGIC MAINE VACATION STAY. This spacious 1903 Masonic Victorian home in the “Prettiest Village” in Midcoast Maine offers 3 bedrooms, 1.5 baths, and is steps from local landmarks like world famous “Red’s Eats” for a lobster roll, boutique shops, antiques, art galleries, and restaurants. Just up the road is the award-nominated “Alna Store”!

The Highland Cottage on Sheepscot

NO HIDDEN FEES THE PRICE IS THE PRICE + CLEANING! Charming, updated, 1920's cottage directly on the banks of the Sheepscot bay. Cottage has - one bedroom with queen bed, bistro table for two, sitting area with sofa and cable television, small convenience kitchen area (no stove), full bath, linens