Vacation rentals in Chocolate Cove

Safe Haven loft Waterfront with Kayaks & Hot Tub

Cute coastal, apartment on the scenic tidal Oak Bay. Relax outside & enjoy the views & watch the amazing tide change, walk on the ocean floor, explore the beach & go kayaking! Lovely space with open living/dining/kitchen area. Master Bedroom with Queen Bed and a small second bedroom w/2 twins! All new memory foam mattresses. Includes use of beach, canoes (2) kayaks (4) BBQ, fire pit w/wood, lawn chairs, pergola, hottub (avail May1-Nov1) , Coffee/tea. Plans for a heated Pool coming July 2026!

Studio @ Chadbourne House: Private deck and more!

Modern studio apartment in a historic building in Eastport Maine. 460 sq ft with private deck, king-sized bed, sitting area w/gas stove, galley kitchen, and bathroom. Walk-out second story deck overlooks large side-yard and has table, umbrella, and chairs for outside dining or simply enjoying the day. Private entrance and off-street parking. Well-equipped kitchen w/ refrigerator/freezer, Keurig, kettle, toaster oven, cookware, knives, utensils, dinnerware. Large closet with vacuum and heater.

Eagles Bluff Cottage

Experience the natural beauty of Maine at Eagles Bluff Cottage, a fully furnished 2 bedroom 1 bath cottage with breathtaking ocean views in Eastport. Relax in the beautifully decorated living room, cook in the fully equipped kitchen, and sleep soundly in the comfortable bedrooms with fresh linens. The modern bathroom has all the amenities you need. Enjoy the peaceful and quiet surroundings from the patio. Book your stay today and experience the magic of Eastport! The home is dog friendly only!

Whale of a View Oceanfront Cottage! Amazing views!

The Whale of a View Cottage has amazing unobstructed views of the ocean and the whales, seals and eagles that pass by the cottage. The Whale cottage is private and sits on a cliff overlooking the water. The cottage also has great outdoor spaces with an attached screened in room, attached open deck and a screened in gazebo located on a lower cliff overlooking the water with open decks. Dining alfresco is easy on the screened porch, open deck or in the screened in gazebo. Enjoy your Stay!

Immaculate tiny house,walk to everything Eastport!

This is a new tiny house, walk to everything.The oceans at the bottom of the hill! Quick walk to the public beach access, and everything else Eastport has to offer.You can be anywhere in town in 5 minutes but located on a quiet street.Such a quaint New England town.You will love this place.Cozy, comfy, has everything you need and then some!Full size shower and tub, big where it counts! Well appointed, nice finishes and linens.Great for a quick visit or an extended stay, you'll love it!Historic

Homestead Cottage downtown Saint Andrews

This private newly renovated suite is perfect for 1-2 people looking to stay in the pretty seaside town of Saint Andrews. Situated away from the street, with ample parking, this suite has comfortable modern furnishings, a fully equipped kitchen and private bathroom, within a short walking distance to downtown Saint Andrews and its many amenities including restaurants, shopping, gardens, museums, walking routes, nature reserves, beaches as well as whaling and outdoor excursions. Come and stay!

Cozy Tiny Cabin on Half Moon Cove

Reconnect with nature at this unforgettable escape. Open concept tiny (home) cabin with king size bed. Couch in living area pulls out to a full size bed. Kitchenette area has an electric cooktop, counter top french door oven, apartment size fridge, Keurig, and amenities to cook/eat/drink. Full separate bathroom with walk-in shower, toilet, sink/ vanity. Dining area overlooking Half Moon Cove. Quiet residential street with ocean view. A spacious deck with propane fire pit.

Historic comfortable in-town one bedroom apartment

Enjoy an early morning stroll, taking in Lubec's beautiful sunrise, while witnessing local fisherman loading gear for open waters. The peaceful town that gracefully lies on the most east point of Maine. Your three minute stroll back to a peaceful in-town one-bedroom apartment, and enjoy a cup of coffee sitting on your own private deck or enjoying a quiet moment in a historic fishing village apartment. Take in all of the surrounding areas and adventurous things to do.

Birch Point Retreat

Experience island living with all the comforts of home in this modern cottage finished in 2025. Wake up in your king size bed to a different view every morning as the tide transforms the landscape from the ocean floor to a 30-foot deep harbour. Watch the wildlife put on amazing shows while you relax or bbq on the wraparound deck. Catch the sunset from huge picture windows or soak in the tub after a long day exploring the acres of private land that surround you.

Mermaid's Mini Mansion

With peak ocean views as well as the first sunrise in the nation from our location across from Todd's Head, the mini-mansion offers a full kitchen, comfortable bedroom, outdoor 3 person hot tub, washer dryer, yard and ocean breezes. Strolling distance to the pier for a whale watch, the artistic downtown, and the brewery! There is a Weber grill, outdoor seating, bikes to use, books, games, record player and WIFI. We welcome your pets and your children :)

The Little Salt Cottage

Welcome to the Little Salt Cottage! Nestled in the charming town plat of St. Andrews-by-the-Sea, enjoy the shops and restaurants of Water Street, stand on the salty ocean shore, and walk along the market wharf...all within two blocks of the home. The perfect East Coast getaway, designed with individuals, couples, and small groups in mind. We hope to host you soon!

The Healing Shack - Escaping your Trappings

Experience an authentic trappers cabin in Maine built in the 1800’s with this unique and tranquil getaway. Private yet within 5 minutes walking distance to the ocean and 2 minute drive to a beautiful lake with boat access. Spacious area for outdoor activities, where children could pitch a tent while the adults enjoy the romantic comforts of a hand hewn cabin.