Holiday rentals in Castine

The Penobscot River Ranch Guesthouse

This unique four season property sits across from conservation land on the Penobscot River in Prospect Maine. There is a 1/2 mile trail down to the river, great for hiking and snowshoeing. An awesome place to unwind with easy access for exploring mid coast and Downeast Maine. Less than 10 minutes to Rt 1 and The Penobscot Narrows Bridge and Rt 1A, 18 miles to Belfast, Castine, Blue Hill, Ellsworth. About an hour to Acadia NP and 45 min to Bangor. Great views of the land, river and wildlife.

Captain’s Quarters By The Sea

Enjoy a serene stay at this classic “on neck” cottage in the heart of everything Castine has to offer. The Captain’s Cottage sleeps up to 8 comfortably and offers plenty of space for restorative activities, relaxing between outdoor pursuits, and remote work (if you must). Start your day with coffee on the front porch and wind down with dinner al fresco watching the sunset. Walk to beaches, Witherle Woods, shopping, dining, museums, & more. MMA Students: House is full for 2025-26 school year

Lavender by the Sea

The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

New enchanting retreat near Acadia National

The camp is brand new on 27 acres of land 3 min to Blue Hill Mountain and 5 min to Blue Hill downtown which is right on the water of The Blue Hill Bay. This is an edge wood enchanting retreat perfect for two to hear birds, squirrels and porcupines. Remember to pick some blueberries when it is in season before the black baby bear down the road eat them all. 3D nature is unfolding right in front of your eyes and Acadia National Park is 50 min drive from here. Oh man, you are free! 编辑

Sea Pearl

This is a Water Front property, unique and tranquil getaway. Newly renovated 2025, this is a perfect spot for your serious fun. Located on water in Penobscot. Bird watchers take notice, watch the eagles soar over head out your door, visit the many islands & see the Puffins, Whale watch. Lots to do kayaking, hiking and lot more! Or just relax in a stunning natural setting on the hammock under the apple trees. Just a short drive to Acadia National Park & Bar Harbor. See you soon.

Luxury Coastal Maine 2BR Apt, 2nd Fl Stunning View

The entire building was completely and structurally remodeled and everything is new. Each unit has new floors, walls, lighting, HVAC, kitchens, bathrooms, bedrooms, and brand new mid-century modern furniture throughout. These are truly designed and built as luxury short term rental units. It's location is perfect to explore greater Penobscot Bay region, Acadia National Park, and it sits in the heart of mid-coast Maine. It is beautiful, friendly, and a perfect place to be.

Penobscot River Views - Two Room Suite!

Two room suite on the first floor of my home with an en-suite private bathroom and views of the Penobscot River/Bay! ***Just under an hour drive to Acadia.*** Convenient access right on Route 1. A short walk to the Sandy Point beach park. Comfortable queen bed and sleep sofa. Two 40” HD TVs with Roku. Mini fridge, microwave, toaster oven and induction burner in room. Almost 400 SF of space! If you need more beds, please see my listing for the room upstairs.

Cozy cottage in the woods

Cozy cabin set in the woods surrounded by fields. The perfect place for a romantic getaway, or to reconnect with friends and family, unplug and relax. Get cozy by the wood stove on chilly nights, or star gaze while you make s’mores by the fire-pit. Our place is just a few minutes drive to the ocean and great hiking trails. We are located very close to historic Castine and Maine Maritime Academy, and about one hours drive from Acadia National Park.