Holiday rentals in Rocky Neck

4.93 out of 5 average rating, 159 reviews

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

4.97 out of 5 average rating, 129 reviews

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

4.96 out of 5 average rating, 122 reviews

Flat in Gloucester

Beautifully remodeled unit in heart of Gloucester

Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and location for your visit.

4.91 out of 5 average rating, 204 reviews

Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2025! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

4.98 out of 5 average rating, 83 reviews

Overlook Gloucester's Inner Harbor, Walk to Town

VACATION or WORK or a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all things is the sunroom chaise overlooking the harbor, but there are also two spacious desk areas including one in the living room which can be closed off for privacy while your family enjoys the rest of the house! (Then, of course, go to the beach!) Flexible cancel policy. We clean & disinfect with a passion that considers you 'family'. Vaccinations preferred.

5 out of 5 average rating, 43 reviews

The Mariner|Family Friendly|Backyard|Walk 2 Beach

KEY FEATURES: ☀ Sleeps 8; 3 bedrooms, 1 king, 1 queen,+ 2 twin ☀ Comfortable queen sized pull out sofa ☀ 2.5 Newly Renovated Bathrooms ☀ Modern and well-equipped kitchen with seating for 6 guests ☀ Fully fenced in backyard and patio with new grill and plenty of outdoor seating ☀Central AC for hot summer days! ☀ Hi-Speed WiFi and Roku Smart TV ☀ Screened in porch ☀ Beach umbrella, chairs, cooler, and beach cart in the shed for your enjoyment ☀ Primary suite with King Bed

4.94 out of 5 average rating, 124 reviews

Flat in Gloucester

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

4.97 out of 5 average rating, 454 reviews

Cabin in Rockport

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.

4.99 out of 5 average rating, 114 reviews

Apartment in Gloucester

3BR Oceanfront Condo with decks

Have fun with the whole family at our stylish oceanfront condo. Capture exquisite sunrises and sunsets off of the decks overlooking the ocean. Spend time in the spacious arcade/game room with family and friends or listen to some smooth beats using our retro record player. Walk to downtown Gloucester where you will find a number of restaurants and bars or alternatively walk to exquisite beaches or parks all available steps from your front door.

Superhost

5 out of 5 average rating, 3 reviews

Stay at Smith Cove

Rare Gloucester Waterfront Retreat! ✓ Nestled above the scenic Smith Cove in Rocky Neck with breathtaking harbor views ✓ Spacious deck with outdoor dining overlooking Smith Cove ✓ Open-concept layout with 17-foot ceilings and expansive windows ✓ Loft-style bedroom & living area overlooking a stunning water view A one-of-a-kind escape—book now! Visit @stay_collections on IG to explore our property gallery and local recommendations!

4.95 out of 5 average rating, 115 reviews

Apartment in Gloucester

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!