Holiday rentals with outdoor seating in Waldoboro

‘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.

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.

Look! River Run Cottage on tidal salt waterfront

Maine the way life should be is not just an expression at River Run its a way of life. Located in Andrew Wyeth country (town of Cushing, Maine) River Run is a recently renovated 600 square ft cottage 75 ft off the St George river. It sits on 260 feet of privately owned tidal salt water river frontage just miles upriver from the Atlantic Ocean. Great for a romantic get away or to reconnect and recharge. Spend your time on the shore or sight seeing in the near by towns of Rockland and Camden

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!

The Adams Suite on U-pick Blueberry Farm

Our one-hundred acre farm is located in the small rural village of Washington. It is located just 2/10 of a mile from the village center where the general store, village church, library, and town offices are located. Beautiful Washington Pond boat landing is only 4/10 of a mile away. Easy commute East (30 minutes) to the coast and must see towns of Rockland, Rockport and Camden or West (30 minutes) to our capitol Augusta. One hour and forty minutes to Bar Harbor and Acadia National Park.

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!

Private Guest Suite in Midcoast Maine

A spacious, serene & private guest suite room with original details, private bathroom & king bed. In a historic Sea Merchant's house, this can be your home base as you explore the Midcoast & Penobscot Bay. Take a short drive to the surrounding coastal villages of Camden, Rockland, Damariscotta & more. Situated on a quiet road, 2 min. drive from Rt 90 (less traffic) & Rt 1, which will take you up & down the lovely coast of Maine. See our guidebook for recommendations!

Little Apple Cabin on 5 acres, amazing stargazing!

Little Apple Cabin is a private tiny cabin on five wooded acres, created for guests who want quiet, space, and deep rest. Surrounded by trees and farmland, it’s a simple, intentional place to slow down, sleep well, and enjoy Maine without crowds or noise. The cabin features a king bed on the main level, a cozy wood stove, and a wrap-around cedar deck for coffee, reading, and stargazing. Camden and Rockland are about 25 minutes away, and Belfast is about 30 minutes.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

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.

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.

"Ship Shape": waterfront, cozy studio- downtown

Located in a historic 200 year old building "Ship Shape" is close to downtown but on a quiet tree-lined residential street. It is just one block to the library, bookstore, post office and all the lovely shops. It is on the shore of the Damariscotta River with wonderful views from inside and out.. You’ll love my place because of the neighborhood, the light, the outdoor space, and the comfortable bed. My place is good for couples and solo adventurers.