Holiday houses in Manchester-by-the-Sea

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

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

Harborfront Retreat on Bearskin Neck

Experience true waterfront living at this private retreat perched directly over Rockport Harbor. Enjoy coffee on your patio as boats drift by and take in peaceful harbor views from one of Rockport’s most iconic locations. Step outside to beaches, art galleries, boutiques, and fresh seafood dining — all just moments away on foot. Perfect for couples or small families seeking a relaxing coastal escape. Inside, historic charm meets modern comfort with exposed beams, a welcoming living space, and

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! ⚓

Peaceful, 1888 Mediterranean Manor by the Beach

Architectural charm in this newly renovated, eco-friendly guest suite, could be a destination in itself with a granite kitchen, open living/dining, large yard, patio, private outdoor fireplace and fountain, and brick courtyard. A block away are beaches, lighthouse, playgrounds and a seaside park. Beverly has historic theatres, top-notch dining, cafes and microbrews. Boston is conveniently 30 mins away; other attractions like museums, castles, trails, water sports and whale watching are nearby.

Springtime waterviews in downtown Rockport

Come to Rockport this spring and stay at this renovated waterfront apartment in a historic home with onsite parking, yard and a private entrance. Our prime downtown location is steps from beaches, restaurants, coffee shops, live music, and shopping on Bearskin Neck. 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.

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.

Mary's By The Sea

A unique 650 square foot ground floor apt across the street from Front Beach. 6 minute walk from the Rockport MBTA . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is best for teens or smaller kids . There is a bathroom with a sink and toilet. There is another room with a sink and shower. The kitchen area is more like a kitchenette than a full-size kitchen. We provide one parking spot next door at The Cove parking lot.

Beverly Farms Apartment “Homeport”

"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and is nearby “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

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, 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!

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit just minutes from Singing Beach. This updated suite offers a clean, modern layout with fireplace, comfortable sleeping space, and is ideal for relaxing stays or remote work. Enjoy a secluded backyard—rare this close to the beach. Located in Manchester-by-the-Sea near downtown, dining, and coastal views. Private entrance, free parking, and fast WiFi. Seasonal pool (5/20–9/8).

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.