Holiday rentals in Rockland Harbor

Simplicity-Just what you need! STR24-20

The first legal tiny house in Rockland! All the comforts of home in this sweet tiny house. First floor living, open floor plan. Small but roomy. In walking distance to Main St, South end beach, the Lobster Festival, Blues Festival, Boat Show and more. You will love the simple concept this little gem offers whether just staying the weekend or for weeks. It is quiet and serene as you sit in the living space and have a warm cup of tea or a cold lemonade. We love our tiny house and hope you do too!

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!

Charming Harbor Private One Bedroom

Situated just above a stream just off Rockport Harbor, this quiet, small one-bedroom apartment has its own private entrance and small deck. Located on the back side of RAYR wine and cheese shop, this charming apartment is within a 10-minute walk of two wonderful restaurants in the village of Rockport, 18 Central and Nina June, as well as a lunch spot and a deli. A wonderful getaway space for couples and solo adventurers, you’ll love it because of the location, ambiance, privacy and charm.

Rockland Relaxing Retreat/AC Walk to Town (25-23)

Walking distance to town! Escape to coastal Maine. Enjoy Rockland’s lobster, vibrant art, and local wine from our comfy 3BR, 1.5BA house—complete with AC. Walk to top restaurants, shops, museums, breweries, and the ferry terminal. King, Queen, and twin/trundle beds; kid & pet friendly; big backyard; full kitchen; smart TV and PS3. Camden’s ski resort is nearby. Book now—military families get 10% off! Coastal charm, great food, and fun await. Parking for two cars on site.

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.

Designer’s Coastal Retreat with Simple Luxuries

A designer’s stunning retreat just a short walk to Rockport harbor. This newly renovated 1920’s one bedroom cottage is tucked into a forested granite hillside with oversized windows to take in the view. Artfully furnished with a minimalist sensibility, the space has been fully winterized in order to be a year round sanctuary. A top of the line steam shower, heated bathroom floor, modern gas fire place, and pigmented plaster walls add touches of luxury.

Sweet Willow Suite, Rockland, private 1st floor

Clean, cozy and quiet, 1-bdrm apartment in Rockland; 1st floor, 1-story separate building, light-filled open area, queen bed, full bath with walk-in shower. Located 1.5 blocks from Main St. Easy walk to downtown and harbor. Suite includes many safety features. Host is hands-on, will greet you at check-in, then respect your privacy. Licensed with the City of Rockland #STR25-6.

A comforting sweet off grid cabin near the beach!

Get away from it all when you stay at our sweet little off grid cabin in the woods. A place where sleep and peace meet! Surrounded by 15 acres of woods and fields and within walking distance to Birch Point State Park, you'll have a perfect little getaway - all while being only a few minutes away from Rockland.

1901 Charm in Downtown Rockland

This sweet house is close to everything, making it easy to plan your visit. Above a storefront, this spacious apartment is in walking distance to shopping, museums, restaurants, the ocean, harbor trail and the boardwalk. Parking on premises, washer/dryer in unit, and AC units.