Holiday rentals in Quahog Bay

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.

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Mermaid's Chair | Private Beach | Hot Tub

*Please note: The hot tub is unavailable from October 27 through April. The booking guest must be at least 25 years old. This classic 1939 Maine camp sits directly on Casco Bay, offering a private dock, sweeping water views, and a saltwater hot tub, all on a quiet road. Properties like this don't come around often, and once you arrive, you’ll understand why. The dock places you right on the water, with one boat slip available for guests. Wolfe’s Neck State Park and Wolfe’s Neck Farm are nearby.

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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!

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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.

Seal Ledge - water's edge cottage with kayaks

Beautiful cottage sitting literally on the water's edge makes you feel like you're staying on a boat (minus the rocking!). Soak up the sun and watch the sun set on the private deck or take a few steps down to the dock and use our kayaks to go visit the seals that hang out on the rocks just down the cove all summer long. The cathedral ceiling great room is all glass facing the water so you can enjoy if it's too cool to sit outside. Only 15 mins to Brunswick and central to everything Harpswell!

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Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax with ocean views, warm up in the sauna or take a refreshing dip. Our cottage is part of Gurnet Village, an over 100-year-old working lobstering & oyster farming property on historic Route 24, between Brunswick & Harpswell. Expect boats, workers, road traffic, gear, and the occasional sounds & smells of a real Maine working waterfront. All rooms have ocean views, with access to the tidal beach & floating dock (May-Dec).

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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.

Tranquility Redefined. The Maine House on Dingley

Available Nov. 1- April 28- 7 Beds - Sleeps 10 Tucked along the rocky coast of Harpswell’s Dingley Island, The Maine House blends comfort with understated seaside elegance. Enjoy sweeping ocean views, then unwind by one of two fireplaces after a day of ice skating or soaking in the hot tub beneath a starlit sky. A chef’s kitchen sets the stage for shared meals, while the pool table, private office, and exercise equipment ensure a cozy, well-rounded winter retreat.

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The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.

Rising Tide Times - quintessential Maine cottage

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!

Maine Coast Retreat | Deep Water Dock + Kayaks

Waterfront retreat in Harpswell with a private deep-water dock—bring your boat and tie up with ease. Launch a kayak right from the property and explore peaceful coves and Maine’s rugged coastline. Enjoy ocean views, fresh sea air, and a quiet, relaxing setting. Perfect for boating enthusiasts or anyone looking to unwind by the water while still close to local dining and coastal attractions.

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Cottage on Todd Bay

Autumn is nearly here, and the maples are turning red along the road down from Bath. Days are warm but crisp, and nights are chilly; our guests on Todd Bay have begun building evening fires in the wood stove. We still have a few more available nights in October for fall getaways -- and we're starting to look ahead to May and the 2027 season!