Vacation rentals in Cherryfield

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Top-rated vacation rentals in Cherryfield

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Guest favorite

A modern kitchen features sleek black countertops and stainless steel appliances, including a refrigerator and stove. The space includes wooden bar stools at the island. Natural light floods the area, highlighted by a rustic brick column and stylish pendant lighting.

Home in Jonesboro

4.94 out of 5 average rating, 140 reviews

The Chandler House with private waterfront.

(Long term discounted bookings available, inquire directly.) This newly renovated 3 bedroom/2 bath home is nestled on the tidal waters of Mason's Bay. The Chandler House boasts "all brand-new everything." We took this 1940's Craftsman Style home down to its studs. Brand new kitchen with with granite counters and all new LG appliances. New washer and dryer. High speed wifi with a 55" smart TV. The large rear deck has a hot outdoor shower. Beyond the orchard is the waterfront with a firepit!

Top guest favorite

The image features the bow of a kayak resting on calm water, with expansive views of the lake extending to tree-lined shores in the distance. A clear blue sky with wispy clouds is visible, creating a serene atmosphere suitable for outdoor exploration.

Apartment in Harrington

5 out of 5 average rating, 10 reviews

Beautiful Waterfront Home Close to Trails & Acadia

This private, waterfront retreat is secluded and peaceful with plenty of space to spread out—right on the water! At high tide, paddle out to Lords Island or take a trip down the peninsula. The local supermarket and gas station are just minutes away, yet the setting is completely rural. Head out to hike some of Maine's best trails or drive to Acadia National Park, The Bold Coast, Jasper Beach, Schoodic Point, or any of the amazing local rivers and lakes. Perfect for couples, families, or friends.

Top guest favorite

A vibrant flower garden stretches along a pathway, featuring a variety of blooming flowers in shades of pink, purple, and yellow. Above, string lights create a warm glow as the sky transitions to evening hues of pink and purple, enhancing the outdoor ambiance.

Apartment in Hancock

4.98 out of 5 average rating, 291 reviews

Flower Farm Loft

When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

Guest favorite

A rustic red barn is viewed from the ground, framed by blooming flowers. A wooden staircase leads to the entrance, with natural greenery surrounding the structure. The blue sky above suggests a clear day, enhancing the peaceful farm setting.

Barn in Franklin

4.87 out of 5 average rating, 116 reviews

Early Riser barn-loft on Organic farm near Acadia

A unique offering for those who want a true farm experience! A clean, rustic above-barn space. Farm animals live below-Winston the roo may crow (early!) Chadde our pet pig may grunt, chickens will cluck! There is a 2 burner stove, cold water sink seasonally(jugs provided in winter) a dorm fridge, and basic kitchen ware. Tea and coffee provided, veg & eggs for sale The shower is at the main house, and a bucket-style compost toilet is in the apartment. There’s a full bed and a fold out couch.

Guest favorite

An open living area features large glass doors that allow natural light to flood the space. A unique wooden table with high chairs is positioned next to a modern kitchen, while a cozy seating area includes a chair and decorative accents against a backdrop of greenery.

Home in Gouldsboro

4.94 out of 5 average rating, 219 reviews

Schoodic Loft Cabin "The Roost" with Kayaks

This playful cabin offers a unique spot to unwind and explore the Schoodic peninsula and Downeast Maine. Kayaks are provided to explore island studded 462 acre Jones pond, a 10 minute walk down a trail. A 10 minute drives brings you to the less visited Schoodic section of Acadia NP, where a network of hiking and biking trails lace the coastal forests and dramatic rocky coast. Nearby Winter Harbor has shops and restaurants and even a ferry across the bay to Bar Harbor and Mount Desert Island.

Guest favorite

An inviting living area features large windows that bring in natural light and offer views of the surrounding forest. A cozy seating area includes a gray sofa and a wooden dining table with chairs. A wooden cabinet adds warmth, while a soft area rug contrasts with the hardwood floor.

Cabin in Eastbrook

4.95 out of 5 average rating, 288 reviews

Hemlock Cabin.

Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scammons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

Top guest favorite

A game of Connect Four is positioned on a woven placemat, set against a backdrop of large windows. The serene view displays the water of Flat Bay and surrounding trees, illuminated by golden sunlight from the setting sun.

Cottage in Milbridge

4.97 out of 5 average rating, 214 reviews

Summer 2025 Waterfront Getaway! Hi-Speed Wi-Fi

Spring 2025 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.

Top guest favorite

A charming farmhouse is surrounded by lush greenery, with a white picket fence framing the entrance. A sign reading 'Butterfish Farm' is prominently displayed, inviting visitors to explore the property. Large windows and a front porch enhance the welcoming appearance of the home.

Farm stay in Cherryfield

4.94 out of 5 average rating, 49 reviews

Farm Stay on a River Close to Acadia, Yoga, Swim

Keep it simple at this peaceful Farm + Yoga Studio. Wake up to deer feeding and birds singing outside your window in a quiet, small town. Take a stroll to the river, walk to the café and visit iconic Maine beaches. Hike & swim nearby, or hang out in Acadia, Blue Hill or Lubec (1 hour away). Your kids are welcome to play on the ninja swing set with our daughter :) Organic coffee, tea & a glass jug for drinking water included. *Note there is NO kitchen*

Guest favorite

A charming cottage is surrounded by trees with autumn foliage. A stone pathway leads to the front porch, which features white railings. Adjacent to the main building, a smaller structure is visible, both set against a backdrop of a grassy area covered with fallen leaves.

Home in Cherryfield

4.97 out of 5 average rating, 29 reviews

Fernwood Cottage

Relax with the whole family at this peaceful place to stay. Located in downtown historic Cherryfield along the Narraguagus River, Fernwood Cottage is walking distance from the general store and local coffee shop. Ten minutes from Schoodic and Tunk lakes and an hour drive from Acadia National Park, Fernwood Cottage is the perfect place to come home to after exploring all that downeast Maine has to offer.

Guest favorite

A modern cottage constructed of natural wood is surrounded by trees and a gravel pathway. It features a small deck with two chairs and a grill, while large windows offer ample natural light. The serene setting enhances the connection to nature.

Guesthouse in Cherryfield

4.95 out of 5 average rating, 20 reviews

Blueberry Cottage

The Blueberry cottage is a recently built guesthouse in a quiet and woodsy setting near our organic wild blueberry field. Centrally located to waterways and hiking in the Downeast region and an hour's drive to Acadia National Park. If you're looking for a weekend getaway or vacationing for a week, this is a great choice. We have all the amenities you will need for a comfortable and cozy stay.

Top guest favorite

A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.

Cottage in Waltham

4.95 out of 5 average rating, 824 reviews

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

Top guest favorite

The image showcases a contemporary home surrounded by lush forest, perched on a rocky ledge. The house features large windows that reflect the natural shoreline and vibrant foliage, while the tranquil water mirrors the landscape, enhancing the serene atmosphere of the coastal environment.

Cottage in Machiasport

5 out of 5 average rating, 136 reviews

Cliff-perched cottage w private hiking trails

Designed to evoke a ship, this stylish 2BD home overlooks the ocean and is surrounded by 30+ acres of woods, wildlife, and area beaches. 12 of these acres include private hiking tails that wend along the water. Hike, kayak, BBQ, explore Downeast working harbors, or just relax on the deck. Enjoy complete privacy just 17 min from town.