Vacation rentals in Westport Island

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.

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.

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

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!

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.

Panoramic Water Views on the Sheepscot

From our living room a wall of windows take in the expansive views of Barter's Island upward to the ocean. Relax on the sunny deck, listen to the birds and lobster boats and watch the seals on the ledge at low tide. Take a walk for breathtaking scenic views of the Sheepscott river. Bring your books, bikes and kayaks. Westport Island offers several preserves for hiking, a local brewery and is a central location to visit many nearby midcoast sights and activities.

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

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!

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

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.