Holiday houses in Harpswell

5 out of 5 average rating, 26 reviews

A serene dock is presented, featuring two aqua lounge chairs positioned beneath a matching umbrella. The water sparkles in the sunlight, with a wooden walkway leading from the shore to the dock. Pine trees frame this tranquil waterfront scene.

Guesthouse in Harpswell

Slack Tide

Relax on the dock at this stylish private guesthouse and watch the sunset over an expansive tidal cove. This waterfront retreat features a private deck with gas grill and fire pit, a full kitchen and living area with fantastic water views, leather recliner, sofa and cable TV. The bedroom has an adjustable king Tempurpedic bed and a luxurious ensuite bathroom with a large shower, towel warmer, led mirror, hand-held bidet, heated toilet seat and washer/dryer. Wake up to breathtaking water views!

A dining table is set with a bowl of fresh salad, complemented by a glass of red wine. In the background, the sun sets over the water, casting a warm golden light through large windows that frame the peaceful waterfront view.

4.95 out of 5 average rating, 19 reviews

Sunset Stunner w/summer dock

Relax with the family at this peaceful place to stay. This cozy waterfront home offers a tranquil escape with breathtaking ocean sunset views that paint the sky each evening. Lots of windows and open concept living area provide uninterrupted vistas of the water, allowing golden light to flood the space. The wrap around deck just steps from the water's edge is an ideal spot for morning coffee or evening dinners as the sun dips below the horizon. This charming home blends comfort and nature.

5 out of 5 average rating, 187 reviews

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

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.

4.99 out of 5 average rating, 429 reviews

The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.

Cottage in Pownal

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.

4.89 out of 5 average rating, 127 reviews

Rising Tide Times - quintessential Maine cottage

Out of State guests please read the Maine State COVID-19 restrictions currently in affect. Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!

4.9 out of 5 average rating, 166 reviews

A tranquil view of the ocean is visible from a spacious wooden deck, featuring several white Adirondack chairs. The calm water reflects the clear blue sky and surrounding greenery, while distant islands can be seen along the horizon.

Cottage in Harpswell

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

4.98 out of 5 average rating, 446 reviews

The two elevated structures of the tree dwelling are connected by a rope bridge, surrounded by lush green trees. Natural materials are utilized in the design, which includes a balcony and multiple levels that create a unique, inviting silhouette against the forest backdrop.

Treehouse in Georgetown

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

4.98 out of 5 average rating, 323 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, 5 reviews

Coveside - Waterfront, Designer Decor, w/Heat & AC

Discover this 2-bedroom 2.5 bath designer home in Harpswell. This fabulous home features beautiful decor with beautiful views; three floors overlooking the water. Both bedrooms with en-suite bathrooms, a sleeper sofa on the lower level, Fidium Fiber and a desk for working remote. A chef's kitchen fully stock with for all your cooking needs. Heat, AC, full size washer and dryer. A Weber grill for enjoying the deck, good food, good drink and the views at any time.

4.95 out of 5 average rating, 478 reviews

The studio's interior displays rustic charm with original rough-hewn beams overhead. A spacious bed is visible in the back area, while a comfortable seating arrangement and TV are situated in the front. Natural light streams through multiple windows, enhancing the welcoming atmosphere.

Guesthouse in Harpswell

Harpswell Studio on Waterview Property! Lobster!

Cottage Style Studio! Clean, spacious, colorful, comfy, bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away. Enjoy the trails in the woods with spectacular views or walk on the beach at one of the state parks! So beautiful!

A serene waterfront view is framed by tall trees, showcasing gentle ripples on the calm water. Three stone benches are positioned in a natural clearing, providing a peaceful space to enjoy the surrounding landscape and vistas of the distant shore.

5 out of 5 average rating, 16 reviews

Modern Oceanfront Cottage on Middle Bay

This brand new modern, two bedroom/two bath cottage overlooks peaceful Middle Bay offering tidal views that bring stunning ocean views and wildlife. This 1,200 open-concept space was designed to maximum the space while maintaining elegance and style. Located in the northern end of the quant fishing town of Harpswell, it is centrally located for quick access to popular destinations such as Bowdoin College, Brunswick, Portland, and Boothbay Harbor.

5 out of 5 average rating, 167 reviews

Tiny home in Georgetown

Near Beach/Hiking+FirePit+S'mores+Pond+Generator

Unwind at Spruce Studio on 8 wooded acres with a pond. * 3 min- Reid State Park Beach & Five Islands Lobster * Private Fire Pit w/S'mores & Wood * Automatic Kohler Generator * Rain Shower * 100% Cotton Bedding & Towels * Heat & A/C * Gas Grill *Spruce Studio is one of two cabins on our 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.

Popular amenities for Harpswell holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Harpswell

5 out of 5 average rating, 9 reviews

A cozy studio space is highlighted by a comfortable queen Murphy bed dressed in soft bedding. Natural light enters through a window beside a wooden armchair and small dining table. A mix of wooden furniture and shelves provides functional storage in a tranquil atmosphere.

Guest suite in Harpswell

Long Point Studio

A single-story house is depicted, featuring a neutral-colored exterior and a welcoming entrance. A paved driveway leads to a garage with double doors. Lush greenery and flower beds surround the property, contributing to a serene outdoor setting.

4.77 out of 5 average rating, 48 reviews

2BR Bayview | Fireplace | Deck | Firepit

4.97 out of 5 average rating, 29 reviews

A charming cottage is situated on a grassy lot, surrounded by tall trees. The building features a wraparound porch and is located near Harpswell Sound, with clear blue water visible in the background under a sunny sky.

Cabin in Harpswell

Waterledge Cottage - Orrs Island, Maine

4.87 out of 5 average rating, 183 reviews

An outdoor patio area is featured with a large glass table surrounded by six chairs. A charcoal grill is positioned to one side, and flowering plants are placed in pots around the wooden deck. Views of the water and trees are visible in the background.

Cottage in Harpswell

Quaint & Peaceful Designer's Oceanfront Cottage

4.93 out of 5 average rating, 215 reviews

A spacious two-story home is shown with a welcoming front porch adorned with rocking chairs. Solar panels are visible on the roof, which is complemented by several skylights. Surrounding greenery enhances the peaceful setting under a partly cloudy sky.

Apartment in Harpswell

Comfortable studio apartment in quiet location

4.98 out of 5 average rating, 59 reviews

The exterior of a two-story home is showcased, featuring a light gray façade with white trim. A spacious yard is visible, surrounded by trees and a circular driveway. A small balcony is located on the second floor, and large windows invite natural light into the sunroom.

Townhouse in Harpswell

Tower Hill House Harpswell, Orr’s Island, Maine

An aerial view captures the beautiful home surrounded by a mix of trees and open land, situated along the serene waters of Harpswell Harbor Cove. The landscape displays a harmonious blend of nature and constructed spaces, emphasizing the home's proximity to the coastline.