Holiday rentals in Harpswell

Seaside Retreat–Breathtaking Views & Ocean Access

Middle Bay Oceanfront Bungalow-- Nestled along the peaceful shores of Wood Landing Cove off Middle Bay, Middle Bay Bungalow offers a timeless escape on Maine’s stunning coastline. Built in 1935 and lovingly maintained by the same family for four generations, this cozy one-bedroom, one-bath bungalow blends rustic charm with unbeatable ocean access—just steps from your front door.t Maine Coastal Connections, based in Harpswell, Maine is excited to be your host for 2026! Same great spot, just a fresh face behind the listing. This beloved getaway is ready for your next adventure—check out what past guests have to say below! Set on a beautiful, private cove, the property presents unbeatable sweeping water views! The bungalow offers direct access for swimming, kayaking, paddleboarding, or simply watching seals play in the water. You're also able to watch Lobsterman pull their traps within your view! Bring your four-legged companion and enjoy peaceful mornings playing fetch on the shore, or Start your day sipping coffee on the screened-in porch as the sun rises over the bay, and wind down in the evening with a cocktail in hand as the sky glows with sunset colors. Inside, the open-concept layout includes a combined kitchen, dining, and living area, along with one bedroom and one full bath. The bungalow also features a cozy screened-in porch, along with an outdoor propane grill, fir pit, and picnic table. Private parking is available on site. A short, few-minute walk brings you to Allen’s Seafood, where you can buy fresh lobster, clams, and crabs straight off the boats. There are also many hiking trails nearby to enjoy, most of them with ocean views along the way! Spend your days exploring the coast, and your evenings dining on the day’s catch by the fire pit or grill. Enjoy meals at the picnic table under the open sky. The small town of Harpswell in the Casco Bay region of Coastal Maine boasts narrow peninsulas and island chains that jut south in the Atlantic Ocean. Harpswell is comprised of areas known as Harpswell Neck, Cundy's Harbor, Great Island, Orr's Island, and Bailey Island. While Harpswell is best known for its working waterfront and unspoiled coastal beauty, it also offers a handful of delightful restaurants, art galleries, and local shops that capture the spirit of Maine. Savor fresh-caught lobster and seafood at casual seaside eateries, explore coastal art and photography by local artists, and browse charming gift shops for handmade goods, nautical treasures, and souvenirs. For outdoor enthusiasts, Harpswell is home to a variety of scenic hiking trails, many of which wind through forests and along rugged shoreline with striking views of the ocean. Keep your eyes out for local wildlife and a variety of coastal birds—from herons and osprey to the occasional bald eagle. Spend the day beachcombing at Stover’s Point Preserve, walking the open space and shorefront at Mitchell Field, or soaking in the peaceful beauty of Curtis Cove. Whether you're setting out on a trail, relaxing on a quiet beach, or enjoying a lobster roll on a dock, Harpswell invites you to slow down and savor the best of Maine’s coast. Just 15 minutes from Harpswell, Brunswick offers everything you need for a convenient day trip or night out—grocery stores, farmers markets, charming boutiques, antique shops, and an impressive selection of restaurants featuring global cuisine. It's also home to a vibrant arts scene, anchored by Bowdoin College, which hosts concerts, exhibitions, and the renowned Maine State Music Theatre, offering professional summer performances in an intimate setting. History buffs can visit the Joshua L. Chamberlain Museum, the former home of the Civil War general, Bowdoin president, and Maine governor. The town itself is set between the Androscoggin River and the coast, offering scenic views and walkable charm. If you're looking to explore further, Portland—with its award-winning restaurants, craft breweries, and coastal culture—is just a short drive away. Other nearby destinations include Freeport (home of LL Bean and outlet shopping), Bath (known for its shipbuilding heritage and the Maine Maritime Museum), the scenic harbor towns of Wiscasset and Boothbay, and even Bar Harbor and Acadia National Park—perfect for a day trip or an extended adventure. Oceanfront Whether you're looking for a peaceful retreat or a romantic coastal escape, Middle Bay Oceanfront Bungalow offers the ideal setting for a couple’s getaway. Its amazing oceanfront location, charming 1930s character, and direct access to the water make it a truly special place to relax and reconnect. Wake up to the sound of the sea, spend your days exploring the shoreline or nearby trails, and end your evenings with breathtaking views of the bay. With the authentic charm of Harpswell, fresh seafood steps away, and easy access to nearby towns like Brunswick and Freeport, this is the perfect spot to slow down, unwind, and experience the best of Coastal Maine. Past reviews of this special property: This is a beautiful spot. It's right on a small cove, surrounded by trees, with a lovely view. We were looking for a place to relax and decompress. This cottage on the bay was perfect. Added bonus is a short walk to Lookout Point, where the sun sets over Middle Bay. Henry Allen and Morse's food truck offer the best lobster you'll ever eat! The host was communicative, yet respectful of our privacy. The cottage is cozy and very well appointed. It looks like it's right out of an L.L. Bean catalogue! Much thought and consideration has clearly been heavily invested in this delightful home. Not only were we peeps happy, but it was a perfect location for us to enjoy our time with our pup. The screened in back porch was a great play area, when we weren’t out exploring coves with her. We are most grateful to Russell for sharing this peaceful spot with others - it is truly a rare find! I just left my third two-week summer stay at Middlebay Bungalow cottage - and it is always a stellar experience for me. I love how close it is to Brunswick, a 15 minute straight shot when returning at night, and how easy it is to get over to explore Orr's and Bailey islands. There are many lovely and easy woodsy trails nearby, most with water views of some description, though it's hard to beat sitting on the porch with a book while watching and hearing the tide come gently in and out. The nearly continuous breeze off the water, with the many fans Russell has available in both rooms, makes this cottage cooler than most summer places are in town. It's a compact, uncluttered living experience, and at the same time Russell and his partner have thought of everything you need to feel at home. Come and enjoy! There really aren’t enough words to describe the serenity of this place. The porch! We lived on that porch! The short walk to Morse’s food truck on opening day was awesome, the proximity to both Freeport and Portland gave us activities when/if we wanted them, and the coziness of the cottage made us not want to leave! I hope to return again soon. Perfect birthday week. Thank you!! The cottage was plenty big enough for me and my dog and had everything I needed. It is a rustic cottage but warm enough with the heater. Very clean , comfy and cozy. I did a lot of reading on the 3-season screened in porch that overlooks the cove and fishing/lobster boats. The TV/wifi worked flawlessly. There are lots of Harpswell Land Trust places to walk and are dog-friendly. For restaurants and groceries Brunswick is a quick drive. I went to a Bowdoin women's soccer game one day which was fun. Next visit I'll check out their art museum. Thank you for sharing this gem of a vacation property. We had the most amazing week at Middle Bay Bungalow. We kayaked and saw seals, a porpoise, tons of birds and their activities. Every day we saw something new and interesting. The cottage was very comfortable, well supplied and clean. Our surroundings were so quiet and peaceful. I cannot recommend Middle Bay Bungalow enough. Thank your for sharing your special place with us. We thoroughly enjoyed our stay at this cabin in Harpswell! The location was astounding-- right on the water, with beautiful views of the ocean. We spent time exploring Brunswick and Orr and Bailey Islands, all a short drive away. The house was everything we needed and very comfortable for two people and a dog. We especially appreciated how well-stocked the kitchen was-- the hosts have thought through everything you'd need to prepare a meal, which was really helpful for a week long vacation. They also provided great recommendations of the area. We will definitely be back and would stay here again without hesitation. Beautiful It was very comfortable sleeping and the views were amazing!! There is much to do around the area and our private beach to launch the Kayak. Having fresh Lobster off the boats was wonderful. The sunsets were very nice, we loved sitting on the porch at night with the ocean breeze. The cottage was clean and we had everything we needed. The communication from the owner was great. I would go again. Lobster with a view. We had a great time. The cabin was cute and cozy, with a beautiful view. Loved watching the lobster boats leave and return. Best part was being walking distance to great food and buying lobsters fresh off the boats. Great place to stay !! Wow The title says it all. To say this was a park like setting on a tidal cove is an understatement. The loudest thing in the neighborhood was the birds in the morning. The kitchen was one of the best stocked we've ever encountered. And my wife loved amenities in the bathroom. The porch was great, so was the grill. We explored the cove and walked over to get fresh lobster for dinner. The short drive to the other areas of Harpswell as well as Brunswick were not overlooked. Overall the hosts were great, check in was easy. We would for sure book again.

Quaint & Peaceful Designer's Oceanfront Cottage

Coco Cottage is a peaceful, cliffside escape with stunning 180° views of Harpswell Sound. Located at the end of a private road, it’s perfect for a designer’s retreat or family getaway. Three bedrooms—two queens, plus a twin/office combo—make it ideal for remote work or rest. Relax fireside and watch a movie, dine on the patio, read on the dock, or explore the amazing trails, beaches, seafood and sunsets of Harpswell. Enjoy oceanfront tranquility just 15minutes from Bowdoin College and Brunswick.

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!

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.

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.

Bayview Suite in Historic Shipbuilder’s Farmhouse

Welcome to the Atlantic suite at the Merrucooneagan: the longest connected farmhouse in Maine! Stylish and cozy, this newly renovated studio has the feel of a Victorian study with stained walnut trim, a stone fireplace, ceiling mouldings, and a large, glassed, built-in bookcase. This unique property features bay views from two porches, 6’ high windows with views of distant pines and expansive meadows, a tiled bathroom with clawfoot tub, and a spacious galley kitchen updated for modern living.

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.

Lovely Coastal Cottage on Quiet Cove

Wake up to gorgeous views and go to sleep under dark starlit skies. This modern and well-appointed coastal home is your chance to experience life on the water in Maine. Harpswell is a beautiful waterfront town with more coastline than anywhere else in Maine. When you're not relaxing on the deck overlooking the cove or, in winter, being cozy by the fire, you'll be able to explore the dozens of hikes on the peninsula and the year-round restaurants in nearby Bath or Brunswick.

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.

Mermaid's Chair | Private Beach | Hot Tub

*Hot tub not available October - April This is a rare one. A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport.

Bird Watching Paradise Harpswell

Gorgeous brand new 1BR in law unit above the garage in a waterfront property with 1.6 acres big lawn! It is so peaceful just to look outside with the big windows or just grab a drink and have some fresh air on the deck. Watch the wild animal crossing the lawn, maybe you will spot a red fox, ducks and geeks are regular visitors :) Also enjoy the Maine wood trails and bay trails around, this is truly a great place for getaway and enjoy the nature!

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.