Holiday rentals in Castine

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 800 Mbs fiber 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. We’re very pet friendly!

The Cabins at Currier Landing Cabin 2: Meadow

Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. The Cabins at Currier Landing, featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest,” are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of the Benjamin River Harbor shore. 2 seasonal cabins; 1 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

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.

Exquisitely Modern Stargazing Cottage @Diagonair

Romantic and luxurious, this 2,000 square foot modern cottage nestled on 12 acres is a favorite of honeymooners and lovers of modern design * 1 hour to Acadia National Park & Bar Harbor; 15 minutes to shopping, hiking, swimming * Stargazing deck * 2 full baths, one with steam shower * Fully equipped kitchen with under-counter fridge/freezer * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

Maine cabin coast & forest Acadia Bar Harbor

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

#1 NE Small Coastal Town- Castine, Shell Cottage

Do you want to go to the #1 small town in the North East? Stay in a thoughtfully designed Maine woods cabin ideally located in a town which offers a true family camp. This Water Street location allows for a picture perfect getaway. Live like a summer person does and learn why they return each season from one generation to the next. Would you choose sailing lessons, golf, tennis, picturesque hikes, kayaking, museums, art classes, farmers markets and more to fill your ideal Maine day?

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.

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

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.

Modern Cabin in the Pines • Hot Tub + Near Acadia

Enjoy our cozy home-away-from-home amid towering pines and granite boulders — the perfect respite after exploring Acadia. Our newly built cabin has rustic Maine charm and modern comforts: AC, waterfall shower, memory foam mattresses, indoor gas fireplace, outdoor gas fire pit, gas grill, hot tub, 4KTV, high-speed internet, modern kitchen, filtered water, gas range, high-end appliances, and front-loading washer/dryer.

Windy Hill Farm

Take it easy at this unique and tranquil getaway. Charming 18th century home in historic Castine, Maine (voted the best small town in the Northeast by USA today) 2 bedroom (1 queen, 1 full). Full kitchen and living room. Private driveway. 5 minutes from downtown dining and shopping 4 minutes from the town beach. 4 minutes from public golf course No pets.

Sea Breeze Cottage in idyllic Castine Maine!

Sea Breeze Cottage, Castine, Maine Experience quintessential New England charm in this cozy Castine cottage. Freshly and tastefully renovated and only a short stroll from beautiful Fort Madison beach. Recharge your batteries and relax to the sound of the nearby bellbuoy! Discover all coastal Maine has to offer from the comfort of Sea Breeze Cottage!