Vacation rentals with outdoor seating in Gloucester

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Top-rated outdoor seating rentals in Gloucester

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Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 389 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

4.96 out of 5 average rating, 267 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

Condo in Gloucester

4.97 out of 5 average rating, 105 reviews

Key West Vibe,PrivatePatio,New Reno,WalkDWNTN

Looking for the perfect Gloucester retreat for your group or family? Look no further than this spacious and inviting 2-bedroom unit, ideal for families and groups seeking comfort, style, and ample room to relax. Step inside and be greeted by a bright and spacious living area, perfect for gathering together after a day of exploring all that Gloucester has to offer. With its comfortable furnishings and modern amenities, this unit is designed to provide you with the ultimate vacation experience.

Guest favorite

Condo in Rockport

4.99 out of 5 average rating, 153 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

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 shops, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport right on Bearskin Neck. Enjoy beautiful ocean breezes sipping coffee or cocktails on the deck of this sweet beach retreat nestled on the Atlantic coast. Come fall in love with charming Rockport!

Guest favorite

Guest suite in Marblehead

4.97 out of 5 average rating, 271 reviews

Private Loft Right on Atlantic Avenue

PETS ARE NOT ALLOWED - CHILDREN UNDER 12 NOT ALLOWED . This is due to Insurance requirements. This private suite is located in the heart of our historic seaside town. Very close walking distance to all Marblehead has to offer, including Devereaux Beach, Seaside Park, historical sites, galleries, multiple restaurants, and shops. Ten minute drive to downtown Salem. This suite is separate from the main house. When my granddaughters stayed over night, they called it their apartment.

Guest favorite

Tiny home in Rockport

4.94 out of 5 average rating, 131 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

Cottage in Essex

4.97 out of 5 average rating, 222 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

Guest favorite

Cabin in Rockport

4.97 out of 5 average rating, 414 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

4.99 out of 5 average rating, 104 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.

Guest favorite

Home in Gloucester

4.97 out of 5 average rating, 104 reviews

Harbor View Walk to Town&Beach, 6 Guests King beds

Home DeepCleaned w Ozone. Newly available for a spectacular Gloucester stay this summer or fall on Cape Ann. From the private oasis, you have a beautiful walk to local beaches & Gloucester center, restaurants, museums, galleries & boutiques, sailing and whaling charters, power boat rentals, SUP, kayaking, historic landmarks, seaside restaurants & also ocean front tennis, boce ball and so much more! This place is a happy haven! ♡

Guest favorite

Guest suite in Rockport

4.99 out of 5 average rating, 623 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Guest favorite

Guest suite in Rockport

4.88 out of 5 average rating, 200 reviews

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.