Holiday rentals in Pennellville

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.

Seaside-The way life should be!

Gentle breezes, fish flipping, seals playing, boats hauling their famous catch of crustaceans…watch it all from the many incredible vantage points this cottage has to offer. From a back patio with a gas fire pit, to a sun porch for enjoying a BBQ lunch, even a screened porch for relaxing when the bugs come out. Join the owners at their “martini bar”next door for added conversation and area knowledge with views! Perfect central spot for exploring the Midcoast.This is truly the way life should be!

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.

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!

Private guest suite in historic Maine cottage

Come enjoy a relaxing stay in the upstairs of a cozy, historic home nestled on the beautiful coast of Maine. The house is within a 2 minute walking distance from Simpson's Point where you can enjoy swimming, picnics, sunsets, and stargazing. You can expect peaceful, quiet days and evenings with the option to bathe in a skylight-lit bathtub/shower and snuggle up in comfy beds lit by twinkle lights. Rental includes entire upper floor with private entrance along with tv/internet (Netflix only).

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.

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

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).

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.

Artsy Hideaway by the Bay

4 night minimum stay. Comfortable apartment with post-modern flair, located on Middle Bay, four miles from Bowdoin College and downtown Brunswick attractions. Glorious views of ocean and islands are a short walk away. The area is a destination for swimming and kayaking. Safe hiking and biking, on open country roads, through the pastoral fields of historic Pennellville. Pets of any kind are not permitted. Please do not send inquiries regarding pets. The unit is kept allergy free.

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82