Holiday rentals with a patio in Gloucester

Oceanfront Retreat

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

Adorable 1-bedroom carriage house

Kick back and relax in this quaint refurbished carriage house, centrally located in Beverly, Massachusetts. The first floor offers a kitchen space (complete with a toaster oven and mini fridge) and a dining area, as well as a spacious living room set that is perfect for nights in after a day of exploring. If you prefer, the patio also has cozy outdoor seating! Upstairs, you can find a comfortable Queen-sized bed, a private bathroom, and a desk space that's perfect for working from home.

Gingerbread House | Downtown | 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, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

CbytheSea - Ocean View Penthouse

Welcome to C by the Sea, our stunning penthouse apartment located in the heart of Gloucester, MA. This beautifully renovated 1 bedroom, 1 bathroom 3rd floor unit boasts breathtaking views of the Gloucester Harbor and Ten Pound Island and features stunning skylight windows, which flood the space with natural light. C by the Sea is located in a charming historic building, built in 1865, sleeps up to 4 people, and is just steps away from all that Gloucester has to offer.

Charming Guesthouse with Access to Private Beach

Private guest cottage in the village of Annisquam, just a 5-minute walk from private Lighthouse Beach. The guest house is separate but adjacent to the main house (which is also available for seasonal rental, including the cottage). Perfect for a couple seeking a quiet stay near friends or family. You will have 1 bedroom and 1 full bath with shower, and access to an outdoor shower. Dedicated onsite parking. The guest house has both heat and an air conditioning unit.

The Salem House | First floor 2 bedroom apartment

Historic 1850 built colonial house with restored exterior and interior odes to Doric order architecture. Originally built for a leather factory owner named Thomas Looby, The Salem house is now a beautiful opportunity to visit Salem in a distinguished space. Exactly one mile from downtown with off street parking, staying here allows being away from the craziness of the city center while intimately experiencing Salem by staying in a historic colonial home.

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!

Smith Cove Cottgage

Escape to the charming Smith Cove Cottage, a beautifully restored boutique, haven situated at the gateway to historic Rocky Neck in East Gloucester, just steps from the picturesque Smith Cove and the Outer Harbor. This seaside gem has been meticulously renovated to seamlessly blend modern comforts with traditional charm, offering the perfect location for relaxation and adventure.