Holiday rentals in Boothbay

4.99 out of 5 average rating, 118 reviews

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

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.

A well-lit space features a spacious bed with white bedding and a small round dining table set for two. A skylight and multiple windows illuminate the room, with scenic views visible through the glass doors leading to a private deck.

4.98 out of 5 average rating, 102 reviews

Penthouse Master Bedroom

The Penthouse is filled with light, lots of windows and skylights. It has two entrances that are both private, one from our deck and another from the main kitchen! It has a large full bathroom, small closet, and a kitchenette with a coffeemaker, refrigerator and sink. All windows, skylights and doors have shades for complete privacy. Book with us from November 14 th through December 31 st and get two complimentary tickets to the Gardens aglow Light show at the Boothbay Botanical Gardens!

The front entrance showcases a vibrant red door framed by two sconces, inviting guests inside. Steps lead up to a spacious deck, which is flanked by decorative flower pots. The house features a classic shingle exterior, accented by charming dormer windows.

4.92 out of 5 average rating, 157 reviews

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.

4.98 out of 5 average rating, 356 reviews

The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.

Cottage in Edgecomb

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.

5 out of 5 average rating, 190 reviews

Cabin in Georgetown

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio 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 & separated by a privacy screen and natural landscaping.

4.92 out of 5 average rating, 236 reviews

Flat in Boothbay

Farnham Point Retreat

New modern apartment over garage. Brand new patio and fire Pit area. Nestled in the woods. 10 minutes from downtown scenic Boothbay Harbor and Botanical Gardens. Near Carriage House Restaurant. Near Ocean Point. Large walk-in closet. Two large flat screen TVs. BBQ Grill, Fire Pit, and outdoor Dining area with table and chairs. Corn hole and ring toss games. Firewood in the shed for guests. Outlet for EV charger available for small fee, upon request.

4.99 out of 5 average rating, 110 reviews

Chic 1-Bedroom at the Heart of Boothbay Harbor

Welcome to Oak Ledge! Stay for Windjammer 2026: June 21-27! Oak Ledge is a beautifully-renovated 2-storey 1-bedroom apartment in the heart of Boothbay Harbor. Bedroom and Bathroom on the upper level. 5-night maximum This is an adults only listing. Sorry, no pets. Our friendly rescue dog "Oscar" roams freely on the property. Off-street parking for one car. Self check-in. Smart TV with streaming - remember to have your log-ins.

An aerial view captures the marina, featuring multiple boats docked along wooden piers. Calm waters reflect the surrounding scenery, while a mix of sailboats and motorboats can be seen. Green trees frame the backdrop, adding to the coastal atmosphere of Boothbay Harbor.

5 out of 5 average rating, 135 reviews

Sail Loft: Oceanfront Apartment on a Pier.

Experience a one-of-a-kind waterfront escape at the Sail Loft in Boothbay Harbor! This unique 1-bedroom apartment is located directly over the water in a working marina, offering stunning panoramic views from every window. It feels like being on a private yacht. Perfect for a couple's getaway, you're just a short walk from all the downtown shops and restaurants. Enjoy a truly memorable stay with free parking included.

Lush greenery surrounds a natural stone pathway leading to a deck. Varied shrubs, including vibrant yellow foliage, are featured alongside purple flowering plants. The wooden deck, partially visible, suggests outdoor seating options that enhance the garden space.

5 out of 5 average rating, 133 reviews

Harbor for Two

Absorbed in ship-building tradition, picturesque Boothbay Harbor is still about boats-boats from around the world bobbing in the harbor, lobster boats unloading the day's catch, sea-kayaks exploring the rocky shoreline. Paddle, shop or gallery-hop along the charming waterfront or discover some of the endless hiking trails.

4.97 out of 5 average rating, 368 reviews

An inviting entrance features a white door with glass panes, framed by red trim. A decorative wheel hangs on the wall, while a flowering planter adds a touch of greenery. Sunlight casts soft shadows on the rustic shingled exterior.

Flat in Boothbay

Sunnymeade

Centrally located close to Boothbay Harbor, East Boothbay and Southport Island. Coastal Maine Botanical Gardens, Boothbay Region Land Trust's 26 hiking trails, Boothbay Railroad Village with live steam train rides and much, much more are great spots to visit.

4.94 out of 5 average rating, 483 reviews

A charming log cabin nestled among lush greenery, featuring a sloped roof and multiple windows. A picnic table is positioned in front, surrounded by natural landscaping. The peaceful outdoor setting invites relaxation and exploration in the surrounding forest.

Cabin in Boothbay

Simple Boothbay Log Cabin on Water

Relax, reflect, & let time stand still when you visit this tiny, off-the-grid (NO ELECTRICITY) log cabin. Lobster bakes, swim, paddle the cove, swing the hammock, enjoy an hypnotic fire and unplug. Looking for pure Maine experience in the Mid-Coast?

4.93 out of 5 average rating, 228 reviews

Cabin in Boothbay

Peaceful & private waterfront cabin

Enjoy uninterrupted quiet on the Maine coast in our light-filled waterfront cabin. Just 5 minutes from lovely Boothbay Harbor for kayaking, sailing, hiking, seafood tasting, you name it! Or just relax at the cabin in a stunning natural setting.

Popular amenities for Boothbay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Boothbay

Superhost

A spacious screened-in porch is framed by large windows, allowing natural light to fill the area. Wooden rocking chairs and a small table are positioned to create a relaxing space surrounded by the greenery of the forest.

Cabin in Boothbay

4.88 out of 5 average rating, 43 reviews

Cheerful 3-bedroom cabin on the Damariscotta

5 out of 5 average rating, 6 reviews

Sea Smoke by Sea Maine

A living room area is presented with large windows showcasing scenic views of Boothbay Harbor. A comfortable sofa invites relaxation, while a small table rests in front. A television is mounted on the wall opposite the windows. Soft curtains frame the view, enhancing natural light.

4.92 out of 5 average rating, 49 reviews

Coastal 1 Bed, 1 Bath, full kitchen w/ harbor view

An aerial view of the Harbourside cottage is displayed, highlighting its proximity to the Boothbay Harbor waterfront. The surrounding area includes various buildings and a parking lot, with boats visible in the water. Ample greenery frames the cottage, enhancing the welcoming ambiance.

4.91 out of 5 average rating, 77 reviews

Cheerful Harbourside Cottage

A modern kitchen is depicted, featuring a large central island with seating for six. Natural light filters in through the glass doors, illuminating the space. Wisps of greenery are visible outside, and pendant lights hang above the island, offering subtle brightness.

5 out of 5 average rating, 24 reviews

Modern Coastal Bungalow • 3BR/2BA • Walk to Town!

5 out of 5 average rating, 22 reviews

Home in Wiscasset

Whisper

4.83 out of 5 average rating, 71 reviews

Lakeview House