Family-friendly holiday rentals in Bristol

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Round Pond Crows Nest Brand new and ready for you!

Newly renovated efficiency apartment with exterior entrance. Roomy bed/living room, kitchenette, private bathroom w/ shower. Comfy bed, a table for two looking out at the big maple treetop (with a few hints of the ocean beyond), kitchenette has a bar sink, fridge for your leftovers/bevys, and a microwave to heat them up! It’s on the 3rd floor, so you’ll be getting your workout! Red chairs on the front yard are for guest use- enjoy the fresh air and ocean breeze! Very clean, bright space.

Cottage on an island on the end of a peninsula N

This is one of two, two bedroom cottages located on Rutherfords Island in South Bristol, Maine. These cottages are next to each other.Our electricity is provided by our grid tied solar array. We are a five minute walk from the Atlantic Ocean, the Damariscotta River, and John's Bay. South Bristol is a small town 14 miles from Damariscotta,where the closest grocery store is located. We are a working fishing village, and lobsters and fresh fish are readily available at the local lobster pounds.

The Byre at Piper’s Pond

The Byre at Piper's Pond is a small farm situated on 80 acres in Bristol, Maine on the Pemaquid Peninsula. The apartment is separated from the main house and has privacy and room for guests to enjoy the area. It is a comfortable rustic contemporary home and setting. We are located a 10 minute drive to Damariscotta. Pemaquid Peninsula is home to the historic Pemaquid Lighthouse, the University of Maine Darling Marine Center, the Old Fort Henry, Pemaquid Beach and beautiful hiking trails.

Cozy Forest Loft (15 min to 3 cute towns)

Bright, cozy loft, surrounded by deep woods, a tranquil retreat offering true peace, separate from our home, w/ its own entrance; we're here if needed. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - woods rich with abundant birds, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. Dogs welcome, no cats due to allergies.

POST OFFICE COTTAGE Pemaquid Point

We now have a social media page! @pemaquidpostofficecottage Enjoy the relaxing, picturesque coast of Maine in this cozy, comfortable cottage...like a dolls house. Centrally located to local attractions, Pemaquid Lighthouse is 1/2 mile walk.Pemaquid beach only a 5 minute drive. Tiny Cottage sleeps two, with a full size bed or use pull-out couch, efficiency kitchen, and compact bathroom , shower stall. ( 16’ x 20’ square footage) Located with access to tide pools, glorious sunsets!

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

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.

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.

Mystical Mary Howe Room, Downtown Damariscotta

This spacious studio apartment is perfect for relaxing after a day of exploring beautiful Damariscotta and surrounding communities. Situated on the third floor of one of Damariscotta's many historical buildings this apartment consists of a large living room area with kitchenette and a separate large bedroom with bath. Parking is right next to the building and a key will be provided for your apartment.

Welcome to "West Winds at Pemaquid"

Take a break and enjoy a stroll down a natural walkway to Coombs Cove off John's Bay. Sit and enjoy watching the tide come in and out or read that book you've been trying to get to for some time. Perfect for the couple who is seeking beauty and peaceful solitude. West Winds was built in 2017 and offers two-bedrooms, full bathroom, living room and eat-in kitchen, laundry and WiFi.