Vacation rentals with outdoor seating in Rockport

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Top-rated outdoor seating rentals in Rockport

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Guest favorite

Condo in Rockport

4.98 out of 5 average rating, 182 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

JUST OPENED NOV/DEC DATES! From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream/coffee, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport on Bearskin Neck. Enjoy beautiful ocean breezes with coffee or cocktails on the deck of this sweet beach retreat nestled on the N.E. coast. Come fall in love with charming Rockport!

Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 420 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2025 monthly rentals. Must Book Summer 2025 via Airbnb website not the APP! *Can't find an opening in SplashLanding? Our 2nd unit SquishInn has openings June-Oct 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples 2 friends can join you!

Guest favorite

Rental unit in Rockport

4.99 out of 5 average rating, 111 reviews

4 Bed 2.5 Bath Water view Downtown with 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.

Guest favorite

Rental unit in Rockport

4.96 out of 5 average rating, 290 reviews

Harbor Retreat | Ocean View | Heart of Downtown

Discover Rockport's Harbor View Apartment! 🌊 This newly renovated 1-bedroom on the second level boasts stunning harbor views from a private deck. Steps from Bearskin Neck, enjoy proximity to unique shops 🛍️, fine dining 🍽️, and beaches 🏖️. Equipped with high-speed WiFi, a 55" Smart TV, and a Murphy couch. Perfect for experiencing Rockport's vibrant atmosphere. Note: Guests must climb stairs and the downtown location can be lively and noisy 🌆. Book your unforgettable seaside escape today! ⚓

Guest favorite

Rental unit in Rockport

4.99 out of 5 average rating, 114 reviews

3 Bedroom Apartment with parking on Bearskin Neck

Built in 1822, the Sound House is conveniently located on Bearskin Neck. The upstairs apartment is renovated with brand new oak floors, new bathrooms, and updated living area. The unit features 3 bedrooms and 2 full bathrooms, with laundry as well as 3 parking spaces in the back of the building. The kitchen includes cooking utensils, with an electric grill and butane burner for outdoor cooking on the new deck overlooking Cape Ann. Enjoy Rockport while creating new memories at the Sound House!

Guest favorite

Condo in Rockport

4.98 out of 5 average rating, 107 reviews

Harbor Place - Airy hideaway over Rockport Harbor

Enjoy stunning views of Rockport Harbor and the Atlantic from Harbor Place, a breezy, quiet open-floorplan bnb on Tuna Wharf, steps from the galleries, shops and restaurants of bustling Bearskin Neck. You'll be within easy strolling distance of several beaches, the train station, the Shalin Liu Performance Center, kayak rentals, walking paths, parks and boat tours. Relax and enjoy the view, eat in or out, lounge on our private beach! Access to Harbor Place is via staircase.

Guest favorite

Tiny home in Rockport

4.92 out of 5 average rating, 146 reviews

Little Red House on Bearskin Neck!

Rockport is a lovely seaside town just 40 miles northeast of Boston at the tip of Cape Ann. It is a small peninsula surrounded by the Atlantic Ocean known for its beaches, seafood, art, and one of a kind shopping. Full of beauty&serenity RCKPT invites you to slow down. Of course you can come explore too! There is no shortage of beaching, swimming, sailing, trailing, kayaking, paddle boarding and diving . The Lil House sits in the center of it all (the neck!) Beauty awaits!

Guest favorite

Home in Rockport

4.97 out of 5 average rating, 318 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

Guest favorite

Guest suite in Rockport

4.94 out of 5 average rating, 123 reviews

The Perfect Get-Away Suite | Near Shops & Beaches

Everything in this suite is new, clean, tidy and modern. There is plenty of natural light and privacy blinds. There is Wifi and HD Cable with Netflix, Prime and other platforms. There is also a kitchenette in the unit with sink, small refrigerator, microwave oven and coffee maker. The house sits on a third acre of land and is fenced in from the road. We are a ten minute walk to the beach and shopping area, and the train station is located only two blocks away.

Guest favorite

Rental unit in Rockport

4.93 out of 5 average rating, 149 reviews

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include wood burning fireplace & deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

Guest favorite

Cabin in Rockport

4.97 out of 5 average rating, 431 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Guest favorite

Guest suite in Rockport

4.98 out of 5 average rating, 126 reviews

Large Suite in the Historic District of Rockport.

This large suite is the entire top floor of a Historic home, approx. 750 sq. feet. Enjoy a short walk to Old Garden Beach , Front beach, Heath’s Tea Room , Shalin Liu Performance Center and all of downtown Rockport many shops, restaurants and art galleries. You will enter your suite via a keyless door up a private “good morning” staircase to the third floor. Includes use of a screened porch, side porch with rockers and grilling area.