Vacation rentals in Castine

5 out of 5 average rating, 107 reviews

A rustic cottage is viewed at sunset, with vibrant hues of orange and pink illuminating the sky. A gravel pathway leads to the entrance, framed by green lawns and decorative flower pots. Trees are visible in the background, enhancing the natural setting.

Guesthouse in Orland

The Greenhouse Cottage

We feel that the best way to describe our getaway to be “Rustic Elegance”. When you walk through the door you will instantly feel the warmth of a uniquely styled Adirondack cottage. Located nearby to the Acadia Highway (aka Route 1), we are close by to historic Fort Knox, Castine, and Acadia. Enjoy our attached “Greenhouse” which has been made over into a delightful screenhouse/patio, the country setting, blueberry fields, and the beautiful sunrises and sunsets! Fire pit, horseshoes, more!!!

Large windows frame a serene view of the water, reflecting soft light. A cozy seating area includes a wicker chair and a couch adorned with striped cushions. The outdoor deck is visible beyond, enhancing the connection to nature.

4.92 out of 5 average rating, 60 reviews

Sweeping Views with Private Beach in Castine

Shore Cottage is a charming, rustic 1904 summer house on the water. Spectacular elevated views over the entrance to Castine's harbor. Watch seals and schooners from the deck or the glassed-in porch, which spans the entire waterside of the house. Descend the stairs and explore the rock pools on your own beach. A pleasant walk or short bike ride takes you to the delightful village of Castine, with restaurants, art galleries, shops. Kayaking, sailing, golf, and tennis are all available in town.

4.98 out of 5 average rating, 129 reviews

A charming cottage is framed by lush green trees and sits along the Penobscot River. The gravel path leads to the entrance, with water visible in the background under a clear blue sky, creating a serene setting for visitors.

Home in Orland

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.

4.95 out of 5 average rating, 138 reviews

Two deer stand in a grassy clearing, surrounded by dense greenery. Their ears are perked up, and they are facing slightly towards the viewer, exhibiting calm curiosity. The sunlight casts soft shadows, highlighting their natural features against the backdrop of young trees.

Cottage in Castine

Castine rustic cabin coast forest Acadia Wi-Fi

Retreating or working remotely here is a dream. Inspiration by wildlife, quiet time, focus and reflection, an incredible secluded ocean beach nearby. The cottage sits off the beaten path, yet is only 2.5 miles from stunning sunsets at the back shore beach. The small bedrooms have comfortable beds with 100% cotton linens and bedding, USB chargers, hi speed WiFi. Large country kitchen is a pleasure to cook in. Adventures-Penobscot Bay, miles of hiking trails, lighthouse & historic forts

4.99 out of 5 average rating, 161 reviews

A quaint cottage entrance is framed by lush greenery and vibrant flowers. White double doors with large windows are accented by a hanging plant. A small bench sits to the side, complemented by colorful blooms in front, enhancing the welcoming appeal of the property.

Guesthouse in Orland

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!

4.95 out of 5 average rating, 227 reviews

A screened-in porch is featured with two comfortable chairs and a coffee table on a textured rug. A wooden bar with stools is positioned against a backdrop of lush greenery, enhancing the serene outdoor connection. Soft natural light filters through the surrounding trees.

Tiny home in Blue Hill

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

4.97 out of 5 average rating, 219 reviews

The exterior of a blue building is shown, featuring a prominent anchor decoration and a sign reading 'Sea Pearl.' Large windows allow for natural light, framing views of the green lawn and water nearby.

Guesthouse in Penobscot

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.

A spacious living area features a light-colored sectional sofa positioned near multiple windows, providing ample natural light. A modern pendant light hangs from the wooden ceiling, and a flat-screen TV is mounted on the wall. Views of greenery are visible through the windows.

5 out of 5 average rating, 32 reviews

Modern Brand New Home with Sweeping Views

Live the Coastal Maine life. This idyllic setting is home to a comfortable, clean modern house that invites relaxing indoor/outdoor living. High ceilings filled with natural light and breathtaking views of Castine Harbor. Come for a weekend, a week-long getaway or stay for a month! Are you a walker? This little village boasts a charming walk around these quiet streets nestled by the water. Easy access to coastal trails, lighthouse, woodland trails, and Acadia National Park.

5 out of 5 average rating, 131 reviews

An outdoor picnic area features a wooden picnic table positioned on a grassy surface, accompanied by a charcoal grill nearby. A charming blue shed stands in the background, with decorative accents on its doors, creating a functional outdoor space.

Apartment in Bucksport

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.

4.99 out of 5 average rating, 129 reviews

A tranquil shoreline along Penobscot Bay is depicted, featuring smooth sand and scattered pebbles. The landscape is framed by gentle hills in the distance under a partly cloudy sky, with reflections shimmering on the water's surface. Vegetation borders the beach, enhancing the natural setting.

Cottage in Belfast

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

4.82 out of 5 average rating, 104 reviews

A gray cabin with a steep roof is nestled among tall trees, featuring a gravel driveway lined with green grass and scattered wildflowers. The entrance to the cabin is framed by lush foliage, creating a sense of privacy and seclusion.

Cottage in Penobscot

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.

4.87 out of 5 average rating, 110 reviews

Three white Adirondack chairs are arranged on a wooden deck overlooking a serene coastal view. The sparkling water is dotted with sailboats, framed by lush greenery and distant wooded islands under a partly cloudy blue sky.

Guest suite in Penobscot

Waterfront Getaway on the coast of Maine.

Cozy waterfront, two bedroom apartment with separate entrance and private deck overlooking the beautiful Maine coast. Walk the shore path through a field, filled with wildflowers, to a private cove on the Bagaduce River. The light filled apartment is located above the garage of a restored antique farmhouse and has beautiful water views from the living room and private deck. The perfect spot for a relaxing vacation on the coast of Maine.

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Popular amenities for Castine vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Castine

The exterior of a historic farmhouse is presented, showcasing a large white building with multiple gabled roofs. Lush green grass surrounds the home, while colorful flower beds add a vibrant touch. A welcoming porch features steps leading to the entrance, framed by leafy trees.

Guest suite in Brooksville

4.83 out of 5 average rating, 140 reviews

Tapley Farm Waterfront Apartment, Acadia, Pets

5 out of 5 average rating, 15 reviews

A large sign welcomes visitors to historic Castine, displaying the name in bold letters. The sign highlights its settlement date of 1613 and is adorned with colorful emblems representing various nations along the top. Lush greenery can be seen in the background.

Tiny home in Castine

Tiny Home w/Loft-Boho by the sea

5 out of 5 average rating, 4 reviews

#1 NE Small Coastal Town- Castine, Shell Cottage

5 out of 5 average rating, 14 reviews

A bathroom corner is depicted, featuring a toilet equipped with a bidet system. Adjacent to the toilet are ADA-compliant arm rails for support. A toilet paper holder with a roll and a small shelf above the toilet add functionality to the space.

Home in Stockton Springs

Coastal Getaway Near Sandy Point

5 out of 5 average rating, 82 reviews

A serene outdoor space features a wooden dining table with matching chairs positioned on a grassy area. A hammock is visible nearby, alongside Adirondack chairs, offering a view of the calm waters of Penobscot Bay framed by lush greenery.

Guesthouse in Searsport

Private oceanfront cottage- Steps to Penobscot Bay

A serene backyard offers lush green grass with a fire pit at the center, surrounded by four blue adirondack chairs. Water views are visible in the background, framed by trees and the charming home nearby.

4.83 out of 5 average rating, 12 reviews

Historic charm with harbor views.

4.83 out of 5 average rating, 12 reviews

1820s Quintessential Maine Cape w/water views