Holiday rentals in Rockland Harbor

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Top-rated holiday rentals in Rockland Harbor

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Top guest favourite
An open living area features a dining table surrounded by black metal chairs, with a cozy sofa nearby. Large windows allow natural light to fill the space, showcasing green walls and a neutral rug. Decorative elements add character without overwhelming the tranquil ambiance.
Flat in Rockport
4.97 out of 5 average rating, 345 reviews

The perfect getaway - Camden/Rockport/Rockland

Bayview Suite is the perfect getaway! Centrally located in Rockport, allowing easy access to Camden, Rockland & Bar Harbor. Country living, yet close to downtown (2.5 miles) without the busy traffic and noise. Located on 20 acres with farmland and live stock surrounding this peaceful and beautiful property. Fresh local farm stands within walking distance. Mountain bike trail on property to reach the area ski lodge & swimming pond. Great for swimming, boating, fishing, biking, hiking & skiing.

Guest favourite
The exterior of the cottage features a light gray shingle facade, complemented by white trim around the windows and front door. A set of three windows with flower boxes is situated on each side of the door. A welcoming porch leads to the entrance.
Home in Rockland
4.95 out of 5 average rating, 426 reviews

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

Top guest favourite
A charming cottage is surrounded by a vibrant display of purple and white lupines. The wooden exterior features multiple windows, allowing natural light to fill the space. Flower boxes adorn the windows, adding a touch of color to the serene setting.
Home in Stonington
5 out of 5 average rating, 52 reviews

Sunlit Cottage on Crockett Cove

Heron Cottage on Crockett Cove Cove Meadow, Stonington Maine Rare September opening: Sept 18-20 (2 nights) * 1 Queen Bedroom/ 1 Full Bath with high quality linens * 2.5 Acres on Crockett Cove's Tidal Estuary * Tandem kayak included! * Firepit, hammock and seating area by the water * 8 minutes to Mailboat Ferry to Isle au Haut (Acadia) * 5 minutes to Aragosta & Barred Island Preserve * Follow us: @covemeadowcottage Also available during the Winter & Spring- please see my separate listing

Top guest favourite
A panoramic view of Rockland Harbor is showcased, featuring numerous sailboats gently sailing on the water. The foreground includes lush green grass and a white picket fence, creating a serene backdrop against the ocean and cloudy sky.
Guest house in Rockland
4.93 out of 5 average rating, 72 reviews

Carriage House on the Harbor

Breathtaking views from the large window and French doors looking directly out at Rockland Harbor and the sailboats floating by. Take it easy at this getaway with a recliner sofa on the patio by the sea. The king suite is everything one needs to unwind. Nestled beside sandy beach park, on the walking trail, boardwalk and beach. Easy walk to downtown. We have two friendly dogs who hang out most of the time in the yard. They love to sit with our guests. Heat pump for heat & air conditioning.

Guest favourite
A rustic cabin is depicted with a sturdy wooden exterior and a covered porch. The porch features a small table and chairs, surrounded by natural foliage and a gravel path. Warm autumn colors can be seen in the surrounding trees.
Cabin in Cushing
4.97 out of 5 average rating, 73 reviews

THE BEAR'S DEN Cute and cozy studio Maine cabin

BROOK & RIDGE CABINS! Come relax & enjoy our immaculate, cute & cozy fully furnished Maine cabin! This little studio retreat is situated on 13 acres on a quiet, wooded parcel yet is convenient to Camden, Rockport, Rockland, and Cushing (Wyeth country). Keyless electronic door lock, basic WIFI; all new appliances (DW, refrigerator, range). W/D on site at no charge. Simple, relaxing, peaceful; perfect for a mini vacation, romantic getaway or weekend adventure! Non smoking, no pets.

Top guest favourite
The exterior of a contemporary yurt is illuminated at night, set among trees in a wooded area. The structure features a circular design with a central roof vent and a wrap-around deck. Soft lighting highlights seating areas on the porch.
Yurt in Appleton
4.95 out of 5 average rating, 349 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. 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.

Top guest favourite
Home in Freeport
5 out of 5 average rating, 16 reviews

Mermaid's Chair | Private Beach | Hot Tub

*Hot tub not available after October 27- April This is a rare one. A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport.

Top guest favourite
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, 209 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own 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.

Guest favourite
Cabin in Thomaston
5 out of 5 average rating, 6 reviews

Granite Meadows: Modern A-Frame with Hot Tub

A-frame couples' retreat with private hot tub. Architecturally bold A-frame cabin: 2 bedrooms, 1 bath, 3 beds, sleeps 4. Fully equipped kitchen, electric fireplace, outdoor hot tub, AC, heating, wifi, TV, washer/dryer, laptop workspace, hair dryer, safety kit. 3-minute drive to Rockland Bay; between Rockland, Camden and Belfast. Car recommended; GPS/direct circular driveway to the A-frame. Ideal for couples seeking coastal access and calm.

Top guest favourite
Home in Owls Head
5 out of 5 average rating, 13 reviews

Extreme Sunrise - Oceanfront Cottage

Eastward is a fully restored waterfront cottage in Owls Head with sweeping views of Penobscot Bay, Rockland Breakwater Lighthouse, and surrounding islands. Set near the end of a quiet dead-end road, it offers rare privacy just a one-mile walk to Rockland’s restaurants and galleries. Enjoy ocean views from both bedrooms, a 4-minute walk to beach access, and thoughtful touches including a coffee bar, granite kitchen, and tile showers.

Top guest favourite
An open living area features a dining table with two wooden chairs, a sofa, and a light-colored coffee table. The kitchen showcases full-size appliances and a window illuminating the space. A warm orange wall adds a touch of character, while bamboo flooring runs throughout.
Guest house in Rockland
4.9 out of 5 average rating, 419 reviews

Sweet Willow Suite, Rockland, private 1st floor

Clean, cozy, and quiet, 1-bdrm apartment. Sweet Willow is downtown Rockland, 2 blocks from Main St. and the waterfront. 1st floor, 1-story separate building, with private entrance, light-filled open area, queen bed, full bath with walk-in shower. Suite includes many safety features. Host is hands-on and is happy to greet you at check-in, then respect your privacy. Licensed with the City of Rockland #STR26-12.

Top guest favourite
Cabin in Rockport
5 out of 5 average rating, 26 reviews

Little Crow Cabin w/Hot Tub

Welcome to Little Crow Cabin! This is a newly built tiny home, placed on a hillside overlooking the trees and forest. With 400 sq ft of indoor space and an equally large deck, you’ll have plenty of space to spread out and relax. You’ll feel tucked away in the trees, while being conveniently located in lovely Rockport, close to all the beauty of Midcoast Maine.

Popular amenities for Rockland Harbor holiday rentals