Holiday rentals with a patio in Gloucester

4 Bed Water View w/ Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

Shore Cottage • Peaceful Coastal Retreat

Tucked away in a quiet, private residential neighborhood, our cozy cottage offers the ideal home base for your Gloucester getaway. Located just steps from the city’s famous boulevard, beautiful beaches, and a variety of local hotspots, you’ll have the best of Cape Ann at your fingertips. The cottage sits behind the main house on the property, offering a peaceful retreat with all the comforts of home. Whether you’re out exploring or simply kicking back and relaxing, this is your place to unwind.

Luxury Portside Townhome Steps to Niles Beach

Escape to Niles Beach and experience the ultimate coastal getaway in our inviting 3 bedroom 3 1/2 bath townhome, just a short walk away from the serene Niles Beach in Gloucester. Perfectly situated for families, couples or friends looking to unwind by the sea. Explore Gloucester's historic harbor and waterfront, discover local seafood dining options and charming shops in downtown or take a scenic walk along Cape Ann's beautiful coastline. Book NOW and Experience the Magic of Gloucester!

Sunset Serenity-Entire Cozy Home-30 min to Salem

Imagine yourself waking up to the waves, enjoying a cup of coffee and watching boats travel between the Annisquam River and Gloucester Harbor. It’s an invitation to an unparalleled waterfront experience. Sunset Serenity offers 1,000 Sq Ft 2 beds 2 baths with one vehicle driveway. Our 1st floor features a spacious kitchen, open concept dining and living area. Upstairs offers 2 bedrooms with water view and full bath with clawfoot tub. Just minutes to downtown and 30 minutes to Salem.

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

Pleasant Place

Pleasant Place is a spacious, clean and centrally located spot to spend time with your family and friends. It has two bedrooms, two full bathrooms and a pull out couch. Sun soaked in natural light, it boasts a newly renovated kitchen, granite island, large dining room and a charming family room with views of the Rockport harbor. Walk downtown, to the beach, or drive around town and take advantage of your own parking spot in the busy summer.

Shoreview Studio on Independence Park & Beach

This historic Victorian residence, is today host to this seaside studio lounge. Once inside, you’ll fall captive to the seascape off Independence Park. The Atlantic panorama provides an awe-inspired sunrise daily. From its elevated perch, the studio has a contemporary feel with its private observation deck to its sophisticated lighting and wet bar design. Comforts include heated floors, air conditioning and powered room-darkening blinds.

Ocean views! Welcome to Sea Breeze! Winter rates!

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family.

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

Downtown Cottage-DeckツParkingツOceanツBeachesツShopsツ

Discover coastal charm at this historic Rockport, MA gem! Breathtaking seaside views, beaches, cafes, art shops, and the Shalin Liu Performance Center nearby. Walk to iconic Motif #1, kayak, hike, or unwind at the beach. Explore nearby Salem, MA, known for its witch trials history, or take a day trip to bustling Boston, just a short drive or train ride away. Experience the best of New England coastal living. Book now!

Charming waterfront home. Patio, AC, Shops, Dining

Discover your dream Rockport getaway! You'll stay nestled on Bearskin Neck, in this cozy harborside condo boasting stunning views, steps from shops, beaches, & galleries. Relax on your private patio overlooking the iconic Motif #1 for your morning coffee or evening happy hour. Book now for a fun getaway, year-round! There is one bedroom upstairs and a pullout sofa downstairs that can sleep 2.

Walk To Downtown and Ocean, Large Private Yard

Private Two Bedroom with Backyard -1 mile walk to historic downtown Rockport; shops and restaurants -1 mile walk to Front Beach, very family friendly -Fast Wifi, 2 Queen Beds, kitchenette with coffee and tea -Quiet, private yard space with firepit - very cozy! -Family friendly space! -Off street parking for 2 cars -Walking distance to town EV chargers Follow us @highsthavenrockport