Holiday rentals in West Gloucester

Guest house in Gloucester

4.96 out of 5 average rating, 269 reviews

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.99 out of 5 average rating, 267 reviews

Loft in Rockport

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England town of Rockport on Cape Ann. The loft is centrally located is literally steps to the beaches, the Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu. 1-min walk to Bearskin Neck & Motif No.1 5-min walk to Front Beach + easy access to many others 8-min drive to Halibut Point Park 25-min drive to Salem 1-hour drive to Boston 15-min walk MBTA Train Station

4.98 out of 5 average rating, 186 reviews

Flat in Rockport

Waterfront Escape! In-town with onsite parking

Brand new waterfront apartment in historic home with onsite parking & private entrance in the heart of town. Views and access to historic harbor from private deck. Beaches, galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck are steps away. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

4.96 out of 5 average rating, 157 reviews

Apartment in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, 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.

4.85 out of 5 average rating, 117 reviews

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

4.98 out of 5 average rating, 384 reviews

Flat in Salem

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

4.97 out of 5 average rating, 117 reviews

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.

4.9 out of 5 average rating, 199 reviews

Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! 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

4.95 out of 5 average rating, 256 reviews

Cottage in Essex

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.

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.

4.95 out of 5 average rating, 108 reviews

Flat in Rockport

Downtown Rockport|King Bed w/Parking|Walk to Train

• Newly remodeled and professionally furnished space! • Steps to Beaches, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu • Private off street parking spot for 2 cars • High Speed Wi-Fi and AC • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • Comfortable KING size memory foam bed • Convenient EV charging right across the street!

4.98 out of 5 average rating, 688 reviews

Guest suite in Rockport

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.

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Other great holiday rentals in West Gloucester

Guest house in Gloucester

4.93 out of 5 average rating, 75 reviews

Charming Guesthouse with Access to Private Beach

JaneRating, 5 stars1 week ago

We adored this adorable guest house. It was perfect for my husband and I as we vacationed in the North Shore. The location was central to all of the nearby towns and their place had everything we needed for our stay. It’s super cozy and quiet on their property. Their neighborhood is one of the cutest we saw during our travels too. If you like to walk, this is one of the most picturesque neighborhoods in Annisquam. The walk to the beach is right around the corner and it’s the cutest little walk. Cat and Lucy were extremely helpful with recommendations around the area and were very responsive to any questions we had. We saw Lucy during our stay and she was super sweet. If you’re lucky you’ll get a little visit from their dog, she’s adorable! We would definitely come back to stay again!!

4.84 out of 5 average rating, 68 reviews

Close to Half Moon Beach!

LesleyRating, 5 stars8 months ago

A lovely and spacious apartment with beautiful views and a warm cozy feel. Walkable to the bay, various trails along the coast, local shops, restaurtants, the waterfront and the train. Sabine was very helpful and considerate when we had some TV issues - which were promptly dealt with along with a gift basket for the inconvenience. Another one followed later for a birthday celebration!! Thank you! I would definitely recommend this location for anyone visiting New England and/or Boston.

4.96 out of 5 average rating, 52 reviews

CbytheSea - Ocean View Penthouse

KaraRating, 5 stars1 day ago

Emily and nicks place in Gloucester has everything you’d hope for in a cape Anne rental… great location, very clean and contemporary, quiet and super comfortable. Easy parking and super proactive and responsive hosts! Thanks so much!

Guest suite in Gloucester

4.94 out of 5 average rating, 88 reviews

Live Like a Local, Just Steps From The Beach

kateRating, 5 stars2 weeks ago

Sue's place is a find. It is lovely and comfortable inside with a terrific view of sunsets over the water. It was necessary for me to do some work while visiting and the WiFi was strong and reliable. The location is ideal: just a brief walk away from Plum Cove Beach and Lane's Cove and a short drive to Halibut Point State Park, Gloucester, and Rockport. Sue is a warm, welcoming host who strikes the perfect balance between being solicitous of and responsive to guest needs and interests and being respectful of guest privacy. I hope to return to Sue's place and highly recommend it to other travelers.

4.85 out of 5 average rating, 99 reviews

Long Beach Suites: Steps Away From Surf!

SamRating, 5 stars6 days ago

This place was perfect for the 1 night stay that I needed while in the area for an event. Exactly as described and had everything I needed. Lucas was a great host and provided plenty of instructions & information beforehand with multiple reminders as my stay approached. I would stay here again.

Guest suite in Gloucester

4.82 out of 5 average rating, 57 reviews

waterview guest suite

AndrewRating, 5 stars5 months ago

Dominique is a great host, and stands out from others in the Gloucester area with her kindness and openness. She welcomed us even though we arrived later than the check in time, guided us to the unit, and made sure that we felt right at home. Her friendliness to our family and our pet is something we really value and appreciate. If you need a cozy riverside apartment within 10 minutes of the lovely cafes and shops of Downtown Gloucester or 15 minutes from picturesque Bearskin Neck in Rockport, this should be at the top of your list!

5 out of 5 average rating, 32 reviews

White Sand beach in a private enclave

EddyRating, 5 stars10 months ago

Great location within walking distance to some of the best beaches in MA. The house is at the highest point in elevation in the area, so every night you had a refreshing breeze from all directions, no need for AC. The host's were friendly, accommodating and responsive. I would definitely stay at the same place again in a heartbeat.