Vacation rentals in Cranberry Island

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Top-rated vacation rentals in Cranberry Island

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Guest favorite

The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.

Treehouse in Appleton

4.97 out of 5 average rating, 393 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favorite

Cabin in Chesterville

5 out of 5 average rating, 148 reviews

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Guest favorite

A bright and clean room features a spacious bed with a light-colored bedspread. A small dining table for two is positioned near the window, offering views of greenery outside. A wooden dresser and a cozy chair complete the inviting atmosphere.

Guest suite in Round Pond

4.8 out of 5 average rating, 138 reviews

Round Pond Crows Nest Brand new and ready for you!

Newly renovated efficiency apartment with exterior entrance. Roomy bed/living room, kitchenette, private bathroom w/ shower. Comfy bed, a table for two looking out at the big maple treetop (with a few hints of the ocean beyond), kitchenette has a bar sink, fridge for your leftovers/bevys, and a microwave to heat them up! It’s on the 3rd floor, so you’ll be getting your workout! Red chairs on the front yard are for guest use- enjoy the fresh air and ocean breeze! Very clean, bright space.

Guest favorite

A serene waterfront scene displays a wooden dock lined with several boats, set against a backdrop of gently rippling water. Bright clouds float in a blue sky, reflecting the tranquil atmosphere of the picturesque harbor.

Apartment in Bremen

4.85 out of 5 average rating, 117 reviews

Lobsterman’s Lodge- Working Waterfront Marina!

Spectacular water views from every window in this 900 sq. ft. 2nd floor apartment built atop a stone seawall on Muscongus Bay. Spacious & affordable home-base in the heart of the Pemaquid Peninsula. You are renting the whole 3 bedroom 30’ x 30’ apartment at Broad Cove Marine. The space includes 3 water-view bedrooms, bath, a large living room with high speed internet, and a well-equipped eat-in kitchen. For a truly authentic Maine maritime experience, Lobsterman’s Lodge is the place to stay.

Top guest favorite

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

5 out of 5 average rating, 181 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favorite

A wooden dock extends into calm water, reflecting the clear blue sky and surrounding greenery. Trees line the shore, creating a serene backdrop for peaceful moments by the water.

Home in Friendship

4.96 out of 5 average rating, 113 reviews

Maine Waterfront Hideaway

You won't find mobs of tourists here but you will experience a working lobstering village in Maine. Sit back, relax and enjoy the quiet and privacy of 2+ acres at the end of a dirt road with a huge dock located on a tidal cove. Great for family reunions with lots of space and activities for folks of all ages. We focus on making the house comfortable and don't want you to worry about the little things like feet on the couch, water rings on the table or a broken glass. Life happens :-)

Top guest favorite

The cozy cottage exterior is illuminated in the evening, highlighted by a bright red front door. Soft light glows from the windows, surrounded by lush greenery. A path with wet pavement reflects the light, creating a welcoming entrance amidst the serene wooded surroundings.

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 424 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Top guest favorite

The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.

Cottage in Edgecomb

4.98 out of 5 average rating, 312 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Top guest favorite

A dining area is illuminated by natural light, featuring a dark wooden table with a decorative centerpiece of fruit. Large windows offer a view of the water and nearby boats, while comfortable seating is arranged alongside the table.

Home in Cushing

4.95 out of 5 average rating, 148 reviews

Dockside Retreat - 2025 booking quickly

This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

Top guest favorite

A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.

Cabin in Georgetown

4.99 out of 5 average rating, 156 reviews

Cedar Sauna+Near Beach+Pond+FirePit

Come relax at Pine Cabin on 8 wooded acres with a pond. * Cedar Barrel Sauna w/Glass Front * Minutes Reid State Park Beach & 5 Island🦞 * Fire Pit w/S'mores * 100% Cotton sheets, towels & bedding * Rain Shower & Heated Bathroom Floor * AC/Heat & Automatic Kohler Generator * SmartTV & Record Player w/Vinyl *Pine Cabin is one of two cabins on our 8 acres. The cabins are 35ft. apart and separated by a privacy screen and natural landscaping making them very private.

Top guest favorite

An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.

Cottage in South Thomaston

4.96 out of 5 average rating, 181 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Top guest favorite

The modern retreat is nestled among trees, featuring a deck with outdoor seating and a picnic table. The structure showcases large windows, allowing natural light to fill the interior, with a welcoming red door standing out against the dark exterior.

Guesthouse in Newcastle

4.98 out of 5 average rating, 117 reviews

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!