Holiday rentals in Harpswell

4.99 out of 5 average rating, 396 reviews

Cottage in Pownal

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

4.95 out of 5 average rating, 64 reviews

Private oceanfront cottage, great views, and float

Cozy cottage on Quahog Bay . Open space Livingroom / kitchen area offers beautiful views of the bay . Second floor is one large bedroom with large windows overlooking the bay. Beautiful recently renovated bathroom with large walk in shower . Wake up to gorgeous sunrises and end your day with a moonrise. Watch a large variety of birds soar over head . Laze on the large deck or walk down to the large private float, go for a swim or venture out on a kayak ride . Enjoy the patio and fire pit area .

4.89 out of 5 average rating, 54 reviews

Basin Cove Retreat: Perfect to explore Mid-Coast

Welcome to our peaceful waterfront cottage on Basin Cove, perfect for year-round relaxation. This cozy 2-bedroom, 1-bath retreat offers serene water views and breathtaking sunsets. Just 12 miles from Brunswick, 30 mins from iconic LL Bean in Freeport, and an hour from Portland, you'll enjoy both tranquility and convenience. Ideal for a quiet winter escape or a summer adventure. The cottage is close to Live Well Farm and Bowdoin College, providing the perfect blend of relaxation and exploration.

4.96 out of 5 average rating, 23 reviews

Home in Georgetown

Breathtaking Bay Views!

Enjoy glorious sunsets over Sagadahoc Bay on Indian Point at the tip of Georgetown Island! Walls of glass bring the outside in to this 3 bed, 2 bath contemporary home where the only decisions you'll make are whether to spend your days at the beach, on the ocean, or exploring the trails... Later in the day you need to choose whether to grill under the stars, take a short drive to one of the great local spots, or head to Five Islands on the wharf for some of the best lobster Maine has to offer!

4.94 out of 5 average rating, 122 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

4.94 out of 5 average rating, 388 reviews

Guest suite in Brunswick

Private Guest Suite in Historic Downtown Brunswick

Welcome to the barn at 64 Federal! Enjoy this private guest suite, featuring its own entry, sitting room, bedroom, private bath, and laundry in a separate wing of this 1838 Greek Revival home. Plenty of light and heat pump/AC. Just two blocks to Bowdoin College and downtown Brunswick. Home on the National Historic Register and directly across from the Harriet Beecher Stowe House. Quiet family of four live in main wing of the house. Suite includes queen bed, pull-out couch and smart TV.

4.95 out of 5 average rating, 462 reviews

Guest house in Harpswell

Harpswell Studio on Waterview Property! Lobster!

Available dates in late June! 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!

4.98 out of 5 average rating, 61 reviews

New Modern Cottage with Ocean Views & Wildlife

The Salty Roost, a modern Scandinavian-inspired guest cottage is positioned on one acre adjacent to our main home in a coastal neighborhood. This property offers distance water views of Middle Bay, dock/water access, on-site parking, grill, hammock chairs, kitchen with all the amenities, WIFI, washer and dryer combo unit, hardwood floors. The cottage is minutes from great restaurants, breweries, hiking trails, and shopping. The most amazing sunsets will surely bring joy to your stay.

4.9 out of 5 average rating, 115 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!

4.91 out of 5 average rating, 116 reviews

Tiny home in Bowdoinham

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

5 out of 5 average rating, 4 reviews

Laurel Shore Cottage - Waterfront, Pet friendly!

This private cottage on the tidal shores of Cundy's Harbor in Harpswell is something you will treasure. You can sit out on the deck in the morning just feet away from the shoreline and watch eagles fly around the shoreline or boats come through the channel when the tides are high. Whether its morning spent with a cup of coffee in hand or dinnertime on the deck it's the vacation "break" you have been looking for. A "pet fee" of $60/night, per pet. DOGS ONLY

4.91 out of 5 average rating, 23 reviews

Cabin in Harpswell

Super-Cozy, Old Town Cabin ~ Relaxing Ocean Views

Take a break and unwind at this rustic, peaceful oasis ! Perfect couples getaway ! Cozy cabin in Harpswell, with picturesque views of the Atlantic. This quaint location is conveniently located as a home base for exploring our Maine coast, or simply just to enjoy our fishing village. Harpswell offers amazing views around every corner, fine shops, restaurants, galleries, hiking trails, as well as preserves, little beaches & the rocky shore !

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Other great holiday rentals in Harpswell

4.87 out of 5 average rating, 157 reviews

Quaint & Peaceful Designer's Oceanfront Cottage

GeorgiaRating, 5 stars3 weeks ago

My partner and I had a lovely stay at this home! It was beautifully decorated and the view was gorgeous, even in the fog. We especially enjoyed the cozy gas fireplace.

4.9 out of 5 average rating, 21 reviews

Overlooking the working waterfront.

NancyRating, 5 stars11 months ago

We really enjoyed our stay at the cottage. The inside looked exactly as pictured. We were immediately struck by the beautiful view we could see of the harbor through the sliding doors and from the back deck. A new dock was being built at an neighboring property and watching the craftsmanship of the builders was fascinating. The bedroom upstairs was lovely with a comfortable king-sized bed and nice bedding. It was lovely waking up to views of the harbor. We would recommend this cottage to others looking for a clean, cozy, and well-appointed place to stay in Harpswell. The cottage was a great jumping off place for our adventures to other parts of Harpswell.

LilyRating, 5 stars2 weeks ago

Cricket Lodge

What a beautiful house and location! We feel so lucky that we found the Cricket Lodge. Nikoline was a lovely and responsive host, and the home was even more charming in person. My friends and I are already talking about trying to plan a trip back. Thank you so much!

5 out of 5 average rating, 7 reviews

Coastal Home away from Home

TerriRating, 5 stars2 weeks ago

This is an absolutely beautiful home! It was very comfortable and had an amazing view from the back porch. The home was very clean and had all of the amenities that we needed. Kathryn was extremely responsive to all of our questions and needs. We would most definitely stay here again if we travel back to the area.

Flat in Harpswell

4.83 out of 5 average rating, 265 reviews

Sunny Apartment on the Ocean.

CarissaRating, 5 stars2 weeks ago

Jane’s place was lovely and peaceful. Check in was smooth and the entire stay was relaxing

5 out of 5 average rating, 5 reviews

Cedar Cottage on Quahog Bay

MikeRating, 5 stars8 months ago

Absolutely beautiful setting over looking a bay full of lobster boats and sailboats. You can enjoy your morning coffee on the deck right outside your den, in some large Adirondack chairs under some trees, or out at the end of a long floating pier. Miles and miles of hiking trails are minutes away. We saw large flocks of turkeys every day within a couple of hundred yards of the cabin. We saw deer and seals on hikes. When you find something like this, there’s no reason to keep looking for something better. You’re not going to find it.

5 out of 5 average rating, 5 reviews

The Point

KristenRating, 5 stars9 months ago

We had a great stay at the point. Everything is wonderful and the pictures don’t do it justice. The house has everything you need and there’s a lot of fun activities and dining in the area. Heather is very responsive and helped answer questions very quickly! Would highly recommend this place and wouldn’t hesitate to book again.