The Yankee Clipper Inn is a 1929 art deco mansion that sits on a rocky bluff overlooking the picturesque Atlantic Ocean in the quintessential seaside town of Rockport, Massachusetts. Our location is conveniently located 3/4 of a mile from beaches and Bearskin Neck the home of Motif Number 1, "the most often-painted building in America." The inn is conveniently located 35 miles north of Boston with a total of 25 guest suites, 8 suites Oceanfront in our main Yankee Clipper building, 10 suites in our Oceanfront Quarterdeck House, and 7 suites directly across the street from the main inn at our Historic Bulfinch House. Most of the suites in all 3 buildings provide stunning ocean views.  The inn offers an ocean-view complimentary full hot breakfast each morning featuring made to order eggs, bacon, sausage, pancakes, and seasonal fruit, coffee, juices, and milk, to get your day off to a tremendous start.  The inn also has an Oceanfront function room and a patio available for weddings, business meetings, or other special events. Our famous guest list includes such icons as President John F. Kennedy, John Lennon, Paul Newman, Bette Davis, June Allison, and countless others who have enjoyed the beautiful grounds, salt-water pool, and our Oceanfront gazebo and special guests like you.

A close up of a tree at Yankee Clipper Inn.

Yankee Clipper Inn

Steeped in history, this traditional early victorian home has been newly remodeled and renovated blending original details and modern design. Pigeon Hill is a two-story vacation rental home featuring a cozy living area and a bright and well-applianced kitchen with sitting area on the main floor. The second floor has two bedrooms, two full baths, and a laundry room. 
Relax and enjoy all that Rockport has to offer. Step out the back door to the quaint backyard and gardens as well as to the path leading you to the Little Parker Pit quarry. Pigeon Cove and downtown Rockport, with its beaches, shops and restaurants, are all within walking distance. 
This property is part of a two-family home with unobtrusive neighbors. The rental unit has a separate entrance and its own parking. 
Tandem parking for two cars in the driveway. 
No pets. No smoking. No events or parties.

A group of lawn chairs sitting on top of a picnic table at Pigeon Hill.

Pigeon Hill

Twin Light Terrace is your home away from home on a quiet cul-de-sac just minutes from downtown Rockport. With bedrooms over three floors, including two living rooms, there is plenty of space for the family to enjoy.

This home is sunny and cheerful, with pops of bright color in every room. The main floor offers a comfortable living room and large eat-in kitchen, with access to the deck. This floor also has a full bathroom and laundry.

Upstairs are four bedrooms and a shared hall bathroom. The King and Queen bedrooms are quite large, with high ceilings and air conditioning. A Twin bedroom and a Full bedroom completes this floor.

The lower garden level has a den with a TV, along with a slider to the tranquil back garden. There is also a full bedroom and a workspace with a built in desk on this floor.

You'll find relaxation in the beautiful terraced back garden with plenty of privacy, outdoor seating and dining, and a gas grill. You can enjoy the peace and quiet of the natural setting while being less than a mile from all that downtown Rockport has to offer.

Twin Light Terrace

Woodfall is a lovely apartment located in a quiet and leafy residential neighborhood just a short walk to Rockport village, with its beaches, shops, and restaurants. Walk inside into a recently updated open-plan kitchen and dining room where cathedral ceilings and a bank of skylights create an airy atmosphere. The sunny living room overlooks the tree-lined garden and hardwood floors gleam throughout.There is a Queen bedroom on the main floor and just up the staircase is a light-filled loft with twin beds and a dedicated work area with a desk. 

The beautifully landscaped private garden has a stone patio and tall pine trees, offering shade. The apartment is self-contained with a private entrance and a separate driveway, offering privacy from the main house (where the friendly but unobtrusive owners reside).  

There is off-street parking for two cars (tandem).

No pets. No smoking. No events or parties.

Woodfall

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 long-term renters with separate entrance and parking. 
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

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 Sunrise on the Cove or, choose to watch the boats go by from just about every room. The home was updated in 2022 with refinished wood floors, new furniture, and fresh, beachy décor. Mini-splits throughout the home keep everything climate-controlled.  

The main floor has two bedrooms, one Queen with water views and another double bedroom. There is also a full bath with a walk-in shower on this level. A Queen suite comprises the entire second floor and includes a sitting area, flat screen TV, and sliders to its own balcony with amazing views. There is a second Queen suite on the lower garden level, with its own full bathroom and deck. The laundry area is also on the garden level.

Sunrise on the Cove is the perfect place to watch the sunrise from any of the decks or while sitting on an Adirondack chair from the waterfront yard complete. Warm up on cool summer nights sitting by the fire pit on the sandy "beach" in the back yard. (Note: Swimming from the property is not allowed, due the rocky shoreline). Come and enjoy your little slice of waterfront heaven at Sunrise on the Cove. Please note that as this is a waterfront property, children should be supervised at all times.

Dogs allowed. No smoking. No events or parties.

Sunrise on the Cove

Newly refreshed in summer 2023!
This updated and well-cared for Victorian home with its captivating ocean views, sits high on two private acres at the end of a secluded lane. The handsome wrap-around porch provides a relaxing spot to enjoy mature manicured gardens, the iconic twin lighthouse towers on Thacher Island, scenic Loblolly Cove and the ocean beyond.
The spacious eat-in kitchen is the perfect gathering area where the designated cook(s) can prepare delicious meals and never lose sight of the ocean. A spacious living room adjoins the large dining room with its generous table and seating for 10. Upstairs, you will find plenty of bedrooms for all the family. 
After a day at the beach, you can enjoy the outdoor shower to clean off the sand. The spacious backyard allows plenty of room for lawn games, outdoor family activities and fun. Walk down to Loblolly Cove where you can put in your kayak or stand up paddleboard or swim at two sandy beaches just a half-mile away. The village of Rockport is just 1 1/2 miles away with its art galleries, antique stores, gift shops, restaurants, a movie theater and the famed Shalin Liu performing arts center. Other enticing attractions include the many granite quarries, Halibut Point State Park, footpaths leading to the ocean and the beautiful rocky coastline. 
ALSO AVAILABLE AS A WINTER RENTAL. The winter rental excludes the third floor and so the home has five bedrooms rather than seven. Two bedrooms available in the winter have queen size beds, two bedrooms have full size beds, and the last bedroom has two twin beds. 
No pets. No smoking. No events or parties.

A close up of a hillside next to a tree at Seacroft.

Seacroft

Experience a relaxing coastal retreat in the historic town of Rockport, Massachusetts, when booking this charming vacation rental! Situated within walking distance of the ocean, this 2-bedroom, 1-bath apartment is the perfect home away from home for those looking to explore miles of beautiful beaches nearby. Take advantage of the convenient location and stroll over to Bearskin Neck to browse local wares or spend your day lounging at Front Beach with your group!
-- THE PROPERTY --
Mass Tax ID: C0332175296 | Pet Friendly w/ Fee | Furnished Deck 
Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Additional Sleeping: Pack 'n Play
HOME HIGHLIGHTS: Smart TV, window A/C unit, dining table, electric fireplace, gas grill
KITCHEN: Fridge, stove, dishwasher, coffee maker, microwave, cooking basics, toaster, dishware/flatware, trash bags/paper towels, blender
GENERAL: Free WiFi, coin laundry on-site, keyless entry, baseboard heating, complimentary toiletries, hair dryer, linens/towels, iron/board
FAQ: Pet fee (paid pre-trip)
SUITABILITY: Stairs required to enter, single story, bathroom is en-suite to Bedroom 2
PARKING: Off-street parking (1 vehicle), free street parking (first-come, first served)
-- THE LOCATION --
COASTAL SIGHTSEEING: Back Beach Landing (0.3 miles), Front Beach (0.3 miles), Harvey Park (0.6 miles), Old Garden Beach (1 mile), Sandy Bay (1 mile), The Whispering Pines (2 miles), Straitsmouth Cove Landing (2 miles), Cathedral Rocks (2 miles), Loblolly Dive Site (3 miles), Pebble Beach (3 miles), Halibut Point State Park (3 miles), Good Harbor Beach (4 miles), Plum Cove Beach (4 miles), Long Beach (5 miles)
LOCAL FUN: Mill Pond Park (0.2 miles), Whale's Jaw (0.3 miles), Rockport Art Association & Museum (0.4 miles), Rockport Music-Shalin Liu Performance Center (0.4 miles), Dogtown Square (7 miles)
GREATER AREA: Gloucester (5 miles), Hammond Castle Museum (7 miles), Essex (11 miles), Manchester-by-the-Sea (12 miles), Castle Hill on the Crane Estate (17 miles)
AIRPORT: Boston Logan International Airport (47 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/ $125 fee (+ taxes & fees) 
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The property requires exterior stairs to access the entrance


A living room filled with furniture and a bed at Lovely Rockport Apartment, Walk to Beaches!.

Lovely Rockport Apartment, Walk to Beaches!

Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage Hill is the perfect vacation destination. Walk to Long Beach (about a 5 minute walk), or take a short drive to Good Harbor Beach. 
 
 Sage Hill is well appointed, with a roomy eat-in kitchen, a breakfast bar and an adjoining deck with comfortable seating – a great place for family and friends to gather. There are 3 bedrooms with AC, two queen and one double, as well as 3 full baths, including a full bath on the first floor. There is also a single bed tucked in a comfortable downstairs room, adding to your flexibility. 
Sage Hill has plenty of outdoor seating, a large lovely deck and yard, a fire pit area, and an outdoor shower to wash the sand off after a day at the beach. The house is privately situated on a large wooded lot. Explore the surroundings of Cape Ann from your private and charming home away from home. Snip some herbs from the garden, watch humming birds at the feeder, toss a book from the library into your beach bag and enjoy your stay.
Dogs allowed. No smoking. No events or parties.

A group of people sitting on a bench in a garden at Sage Hill.

Sage Hill

Enjoy beautiful views of Sandy Bay and the Atlantic from this classic New England vacation rental home on Rockport's Pigeon Hill. Landmark Lookout offers privacy and quiet and fulfills a nature lover's dreams while being just a 10-15 minute stroll into town and to the beaches.
Perched halfway up a hill, our vacation rental is beautifully decorated with coastal hues and tones, and filled with natural light. From the front entrance, step into the bright sunroom then through the French doors into the open plan living/dining/kitchen area. There are two bedrooms, a sitting room, and a full bath on the main living level. Upstairs are two bedrooms, a full bath, and laundry room. 
The large outdoor brick patio is enclosed. Enjoy the serene garden, summer breezes and summer sun while dining or relaxing on the outdoor furniture. 
A swimming quarry is just a few minutes away from the Landmark Lookout. Follow the many well-traveled paths through the nearby woods where you are sure to come across other glittering stone quarries, now filled with fresh water, perfect for summer dips. Take another path to find yourself at a children's playground with adjacent public tennis courts. Discover the local beaches and the village of Rockport filled with restaurants, shops, galleries, a performance art center, and the commuter train into Boston. Your summer adventure awaits!
There is off-street parking for 4 cars.
Dogs allowed. No smoking. No events or parties.

A house with bushes in front of a brick building at Landmark Lookout.

Landmark Lookout

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