Stroll the quaint lanes of Rockport browsing at its many art galleries and boutiques on famed Bearskin Neck. Dine at the many fine restaurants in and around the village. Walk a few short minutes to Front Beach for a day in the sun and salt water or meander over to Mill Pond for relaxation in the cooling shade. History buffs will love to explore the adjacent colonial-era burial ground nearby.

Mill Lane is a bright one-bedroom rental home with high ceilings and decor that is contemporary and comfortable. Walk up a few granite stairs to the main entrance. Enter into the open single-floor plan featuring a cozy living, dining and kitchen space. Continue straight through to the bedroom. Large skylights bring beautiful light into the bedroom. Access the private backyard from the back door in the bedroom for a quiet place to relax outside for morning coffee or after a day at the beach. Enjoy seasonal and peek-a-boo views from the living area. Hardwood floors are throughout the house. 
This property is part of a two-family home with a 4-bedroom house that is also available to rent. 
There is one off-street parking space and no immediate street parking available.
No smoking. No events or parties.

A room filled with furniture and a large window at Mill Lane.

Mill Lane

This sweet vacation rental cottage is a short distance to two of Rockport's finest beaches - Cape Hedge and Long Beach. The cozy summer cottage has lovely views, from the back deck and lush yard, of the marsh and Saratoga Creek which handles the glittering tidal flow from the beaches. 
 
Beach Bungalow is a one-level living vacation rental designed for easy living. You will have everything you need for the perfect beach getaway with the enclosed sun porch for additional living space. The living room has plenty of comfortable seating which conveniently doubles as the dining area. Several rooms are wall-paneled creating a cozy and comfy feel. 
Off of the living area are two bedrooms, a modern bathroom with a shower, as well as the compact but very functional kitchen, which has everything you need. A door from the kitchen leads to the back deck which is set up with outdoor seating including a dining table and grill with views of the water.
Just a short path takes you to the Saratoga Creek Footbridge which leads you to your choice of Cape Hedge (to the left) or Long Beach (to the right). Life should always have such easy choices! Choose to spend your beach vacation in this idyllic spot in Rockport by the sea. 
There is off-street parking for 2 cars in the driveway.

835 Sq. Ft. No smoking. No pets. No events or parties.

Enter the cottage through the bright and cozy sunroom.

Beach Bungalow

From its waterfront perch, this vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to everything you might want, including Front Beach, restaurants, galleries and shops and the world class Shalin Liu Performing Arts Center.  Stroll along the waterfront Atlantic Path, take a hike at nearby Halibut Point State Park, or walk towards the village, stopping at Back Beach along the way.

Enjoy the water views from the deck, porch, and patio that grace each level of the home or from just about every room. You'll enjoy nature's show, the ebb and flow of the tide, with the quiet passing of the lobster boats and their omnipresent gull followers.

The living room, with sliders to the wraparound farmers porch, is open to the dining area and kitchen beyond. This is the perfect place to watch the sunrise (if you choose), from any of the decks or waterfront yard complete with a large fire pit. 
The granite kitchen has stainless appliances and stylish new cabinets.  
The main floor has two bedrooms, one queen with water views and another double bedroom. There is also a full bath with a tub and shower on this level. The second floor is the primary queen suite with a sitting area, flat screen TV and sliders to its own deck with those amazing views. Air conditioning will keep you cool, even on the hottest summer days. The bathroom is separated with a sink and toilet in a separate room and another sink outside in the main room for easy access. 

There is a bonus living and sleeping area on the lower level with a queen bed, double futon and flat screen TV as well as an oversized bath with a shower and laundry room. Sliders lead to the patio and spacious yard, and waterfront fire pit. Come and enjoy your little slice of waterfront heaven at Sunrise on the Cove. Please note that this is a waterfront property; younger children should be supervised at all times. 

Dogs allowed. No smoking. No events or parties.

Sunrise on the Cove

The View is a quintessential one-story New England cottage with stunning views of Pigeon Cove. This rental home has two bedrooms, an open plan living/dining room with a wall of windows looking out towards the ocean, a modern kitchen, and a 3-season glassed-in porch offering an extra sleeping space, and a deck. Air conditioning will keep you cool throughout the house on those warm summer days and nights. 
Enjoy the ocean breezes and stunning views while dining or relaxing on the deck. The outdoor table seats up to 4 and comes with an umbrella providing shade when needed. Grill up your favorite summer meal on the small gas grill. 
Escape to this private coastal paradise with breathtaking panoramic views of the Atlantic Ocean, Granite Pier, Rockport's coastline, and out to the Straitsmouth Lighthouse. Less than a mile from downtown Rockport, explore all that the village has to offer with its galleries, shops, and restaurants, or wander to the beaches, quarries, or parks for some outdoor adventures. 
Dogs allowed. No smoking. No events or parties.

An umbrella sitting on top of a sandy beach at The View.

The View

Gather your crew and escape to the gorgeous shores of Massachusetts when you stay at this charming 5-bedroom, 1.5-bathroom vacation rental. Take the provided inner tubes or paddleboard out on the water, visit Eastern Point Lighthouse, or explore the impressive Hammond Castle Museum. Getting hungry? Return to the Rockport cottage at sunset and enjoy a cookout on the patio. This pet-friendly property also features a sunroom, 2 living areas, and various board games for the whole family!

-- THE PROPERTY --

C0499622520 | Pets Welcome w/ Fee | 2 Living Areas | Sunroom | Outdoor Shower

Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: 2 Twin Beds | Bedroom 5: 2 Twin Beds, Twin Daybed

COMMUNITY AMENITIES: Basketball court, pickleball courts, tennis courts
OUTDOOR LIVING: Patio, outdoor dining area w/ umbrella, grill, inflatable tubes/paddleboard, inflatable kayak, beach chairs/towels
INDOOR LIVING: 2 flat-screen TVs, books, board games, electric fireplace
KITCHEN: Stove/oven, refrigerator, microwave, dishware/flatware, cooking basics, Keurig coffee maker, toaster oven, blender
GENERAL: Free WiFi, baseboard heating, towels/linens, hair dryer, trash bags/paper towels
FAQ: Pet fee (paid pre-trip), no A/C, community gate fee (paid pre-trip)
ACCESSIBILITY: 2-story home, 1 step to enter, 3 bedrooms on 1st floor, kitchen on 2nd floor, steps required to access beach
PARKING: Driveway (2 vehicles), addt'l parking (2 vehicles)

-- THE LOCATION --

BEACHES: Long Beach (50 feet), Good Harbor Beach (1 mile). Pebble Beach (2 miles), Niles Beach (4 miles)
THINGS TO SEE + DO: Long Beach Tennis Courts (walking distance), Cape Ann Museum (3 miles), Maritime Gloucester (3 miles), Rockport Music-Shalin Liu Performance Center (4 miles), Stage Fort Park (4 miles), Eastern Point Lighthouse (6 miles), Hammond Castle Museum (6 miles), Halibut Point State Park (7 miles)
BOSTON DAY TRIP: USS Constitution Museum (37 miles), New England Aquarium (38 miles), Boston Common (38 miles), Museum of Science (38 miles), Museum of Fine Arts (40 miles), The Harvard Museum of Natural History (41 miles)
AIRPORT: Boston Logan International Airport (36 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- Pet friendly w/ $50 fee (+ fees & taxes)
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The property is not equipped with air conditioning
- NOTE: This 2-story home requires 1 step to enter. While 3 bedrooms and a full bathroom are located on the 1st floor, a flight of stairs is required to access the kitchen on the 2nd floor. Additional steps are required to access the beach
- NOTE: A gate pass is required to access the community for a separate fee. Please reach out to the Guest Contact prior to your arrival to obtain the gate passes



A living room at Rockport Cottage w/ Patio - Walk to Beach!.

Rockport Cottage w/ Patio - Steps to Beach!

Welcome to The Rockporter, a beautifully renovated waterfront retreat in the heart of Rockport’s historic Pigeon Cove. Just updated in 2025, this charming coastal home offers expansive views of Sandy Bay and Pigeon Cove Harbor from nearly every room, giving guests a genuine and peaceful Cape Ann experience.

The home comfortably sleeps 7 guests and now features brand-new updates throughout, including mini-split air conditioning units in every room for year-round comfort. The first floor includes a fully equipped kitchen, formal dining room, cozy living area with a wood-burning fireplace, a full bathroom, and a den with TV and sleeper sofa. Upstairs, you’ll find two bedrooms, an artist's studio with sleeper sofa, and a second full bath — all thoughtfully furnished and designed for relaxation. Much of the artwork and photography throughout the home was created by the property owner, adding a personal and authentic touch to the space.

Step outside to enjoy ocean breezes on the patio or head out your front door for incredible shoreline walks. With Halibut Point State Park and Rockport’s Back Beach just a mile in either direction, you’re perfectly situated to explore all that the area has to offer. Watch lobster boats in the working harbor, take in the historic setting, and unwind in the beauty of the North Shore.

 Parking for 2 cars. No smoking. No events or parties.

The Rockporter

Wake up by the water when you book a stay at this well-equipped and welcoming vacation rental in Rockport, MA! Primely located within walking distance from the shores of Long Beach, the fully furnished 3-bedroom, 2-bath home boasts all the basics — like a kitchen, Smart TVs, and free WiFi — and a deck with a dining area perfect for meals al fresco. Soak up the sun, sink your toes in the sand, or enjoy a salty swim! And don't forget to visit Cathedral Rocks and Halibut Point State Park.

-- THE PROPERTY --

MassTaxConnect ID C0428682520 | Free WiFi | Community Basketball Hoop & Tennis Court | 1,200 Sq Ft

Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Living Room: Full Sleeper Sofa | Additional Sleeping: Pack 'n Play

OUTDOOR LIVING: Balcony, seating & dining, forested views, private beach access, beach gear, swing set
INDOOR AMENITIES: Smart TVs, dining table, fireplace, electric heating, high chair, board games & books
KITCHEN: Well-equipped w/ refrigerator, ice maker, microwave, dishwasher, dishware/flatware, stove/oven, cooking basics, coffee maker, blender, toaster oven
GENERAL: Linens/towels, window A/C unit, ceiling fans, hair dryer, hangers, iron/board, trash bags/paper towels
FAQ: Outdoor staircase required to enter
PARKING: Driveway (3 vehicles)

-- THE LOCATION --

SUN & SAND: Long Beach (walking distance), Good Harbor Beach (1 mile), Pebble Beach (2 miles), Old Garden Beach (3 miles), Back Beach Landing (4 miles), Front Beach (4 miles)
OPT OUTSIDE: Loblolly Dive Site (2 miles), Straitsmouth Cove Landing (3 miles), Harvey Park (4 miles), The Whispering Pines (6 miles), Cathedral Rocks (6 miles), Halibut Point State Park (7 miles)
LOCAL FUN: Mill Pond Park (4 miles), Rockport Art Association & Museum (4 miles), Rockport Music-Shalin Liu Performance Center (4 miles), Whale's Jaw (5 miles), Dogtown Square (5 miles)
GREATER AREA: Gloucester (3 miles), Hammond Castle Museum (6 miles), Essex (10 miles), Manchester-by-the-Sea (10 miles), Castle Hill on the Crane Estate (16 miles)
AIRPORT: Boston Logan International Airport (36 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property requires using an outdoor staircase to enter



Inviting Rockport Rental w/ Deck: Walk to Beach!

Get away to this modern two-bedroom apartment located in the heart of downtown Rockport. With ocean views and decks on two floors, you get a bird's eye view of Main Street, Front Beach and the Atlantic Ocean.

Portside Overlook is a bright and charming, newly renovated apartment offering an open plan living/dining/kitchen area and central air conditioning. Filled with light, it is a great place for a relaxing retreat. The apartment includes laundry, and two private decks.

Walk just a few steps to Main Street where you can explore the restaurants, shops, galleries and more. Around the corner, less than .2 miles away, you'll find Front Beach, where you can go for a swim or hang out in the sand.

When you're ready to relax at home, simply step out to either of the two decks where you can enjoy the sunshine, dine outside and look over Downtown Rockport, Front Beach, and the sea beyond.

Please note that this a two floor apartment on the third and fourth floors of a three-family building with two other apartments below it. The main door to the building is shared with the second floor unit, but you then have your own private, locked entrance.

No smoking. No events or parties.

A chair sitting in front of a building at Portside Overlook.

Portside Overlook

This gorgeous in-town Victorian vacation rental home offers the best of all worlds, blending old-world charm with a fun, eclectic LA/Hollywood theme that reflects the music industry throughout its decor. From photos of legendary musical artists to movie posters, this home is a perfect mix of elegance and playful style. Pleasant House has been beautifully renovated, retaining its old-world charm that features 14-foot ceilings, large windows, and big rooms. Modern updates include updated baths, windows, refinished hardwood floors, walls, and woodwork.
The house is perfectly situated just a short walk to Rockport Harbor, two beaches, restaurants, galleries, shops, and the world-renowned Shalin Liu Performing Arts Center. This is the spacious and perfectly located Rockport vacation home you have been looking for. 
Pleasant House in Rockport has two living areas -- a family room with a large flat-screen Smart TV (with a complimentary Netflix account) and plenty of comfy seating, and a living room with large windows and a sectional sofa. The formal dining room seats at least 10, and the large eat-in kitchen has a large butcher block center island, fine Silestone counters, a dishwasher, and a washer & dryer. Off of the kitchen is a sunny, air-conditioned guest suite with a queen bed and ensuite full bath with shower. Also accessible from the kitchen is one of the best features of the house -- a huge screened porch that serves as another living area, game area and shady place to eat and relax.  
To get to the second floor, you have your choice of two staircases – the formal and gorgeous antique spiral, or the back stairs from the kitchen. Upstairs are 3 more air-conditioned bedrooms, all with connecting full baths.  
Pleasant House offers plenty of room for family and guests to spread out inside and out in the verdant yard and gardens. 
There is off-street parking for 2 cars with plenty more available on the street.No pets. No smoking. No events or parties.

Pleasant House in Rockport

Portside at Front Beach is newly renovated 3-family home offering three distinct private units in a historic building in the heart of Downtown Rockport. Complete with three decks with ocean views, a spacious backyard and central air conditioning it is the perfect place to bring your group.

Great for families travelling together or groups who want to spread out. Portside offers four queen bedrooms and four bathrooms over four floors. With three units that can each be rented separately, you can take your pick of where to stay (see Portside Walkabout, Portside Glimpse, and Portside Overlook). Each apartment has a kitchen, laundry and a full bathroom for each of the bedrooms.

Walk right into the ground floor one-bedroom apartment with a slider to the patio and easy access to the spacious yard. One the second floor you'll find an almost identical apartment with a small deck where you can catch a glimpse of the Atlantic Ocean. The top unit on the third and fourth floors has two bedrooms and two bathrooms. Take your pick of decks to relax on while you overlook downtown Rockport and Front Beach.

When you're ready for an adventure just walk a few hundred yards to beautiful Front Beach or to the shops, galleries and restaurants of downtown Rockport and Bearskin Neck.

No smoking. No events or parties.

Three separate apartments in a four-story historic home

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