Holiday rentals in South Bristol

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.

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

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). Starting January 2025 we will no longer allow pets.

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!

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.

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!

Linekin Guest Suite

Tucked away guest studio attached to main home that you will have all to yourself with basic amenities and a sky lighted bathroom. A few minutes to Ocean Point and hiking trails and less than 10 minutes to Boothbay Harbor. **Please note there are stairs that need to be climbed on the front deck in order to access the property. Use the directions provided as your GPS sometimes puts you in a circle around Boothbay!