Holiday houses in Manchester-by-the-Sea

Stay at Little River

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Waterfront setting on peaceful Little River with private dock access ✓ Sleeps 7 across 4 bedrooms: king, queen, and 3 twins ✓ Fully renovated with bright interiors, central AC, and modern comforts ✓ Outdoor patio with dining, lounge seating, grill, and river views ✓ Minutes to Stage Fort Park, downtown Gloucester, beaches, and trails See more photos, video tours, and local recommendations on IG

Family · Location · Sleep quality

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.

Family · Location · Walkability

Blue Magnolia

High in the treetops, this spacious apartment is only two blocks from the Atlantic Ocean! You'll enjoy 1400+ square feet with beautiful hardwood floors, an all-new kitchen, and your choice of two comfortable bedrooms -- one king and one queen. With a sleeper sofa, the apartment can sleep six total. This is a 2-flight walkup with private entrance, plus access to a large patio and well-established plantings including roses & a grassy yard. Offstreet parking in back if needed, thru driveway gates.

Location · Family · Checkout

Traditional Cape Home with Old-World Charm

This inviting Manchester-by-the-Sea cottage blends modern updates with timeless New England character. Located near downtown, it offers a full kitchen with a dedicated dining area, a cozy living room, and a spacious first-floor primary suite with a private bath. Upstairs are two comfortable bedrooms and a full bath. Additional highlights include first-floor laundry, off-street parking for 2–3 cars, and a charming yard with outdoor dining and a barbecue grill available from spring through fall.

Location · Sleep quality · Beach

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.

Location · Family · Condition

Stunning Ocean-View Retreat, Magnolia Beach

Escape to this luxury coastal retreat home overlooking the Atlantic ocean. Stunning newly renovated 2-bedroom, 2-bathroom apartment, offers 1,500 sq feet of bright and sunny living space. Free off street parking for two cars included. Bedrooms both have king size beds. Fully equipped kitchen with high-end appliances. Cable TV & WiFi included. Washer and dryer in unit. Located near Magnolia beach, Coolidge Reservation, Hammond Castle, Stage Fort Park. Beauport Hotel, downtown Gloucester.

Location · Indoor spaces · Walkability

Coastal 1BR • Singing Beach/Village • Private Yard

Settle into your private coastal retreat in the heart of Manchester-by-the-Sea. Walk to village cafés, restaurants, shops, the harbor and commuter rail, or walk to beautiful Singing Beach. Back at home, relax on your private deck and backyard, start the morning with espresso, and enjoy the convenience of off-street parking for two cars. It’s an easy North Shore home base for beach weekends, exploring Cape Ann, day trips to Salem/Rockport/Gloucester, or taking the train into Boston.

Value · Location · Bathroom

Oceanfront Retreat w/ Deck & Parking

• Private deck with ocean view • Parking • Steps to Front Beach • Walk to Bearskin Neck • Pet friendly • 15-minute walk to commuter rail • Contemporary art gallery on site Beautifully renovated, light-filled top-floor apartment on the water in historic downtown Rockport. Enjoy a private ocean-view deck, one dedicated parking space, and seasonal private access to Front Beach. One of three guest apartments at The Pearl, located just behind Thalassa, our contemporary art gallery.

Family · Location · Quiet

Modern Studio Beverly – Private & Peaceful Retreat

Welcome to your quiet getaway in the heart of Beverly, MA. This stylish, modern minimalist studio is perfect for solo travelers or couples seeking comfort, convenience, and a touch of calm. With a private entrance, full bathroom, and space designed to inspire focus or relaxation, it’s ideal for both short stays and work-from-anywhere escapes. 🚫 Please Note: NO smoking - NO pets Book your stay and enjoy a peaceful home base close to beaches, coffee shops, art, and adventure!

Family · Value · Access

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit, minutes from Singing Beach. This updated suite features a modern layout, fireplace, and two queen beds—one in a private sleeping area. Ideal for relaxing or remote work, with a secluded backyard, private entrance, free parking, and fast Wi-Fi. Near downtown Manchester-by-the-Sea, dining, and coastal views. Seasonal pool: 5/20–9/8. Walk to local shops, restaurants, and the harbor, all from this peaceful setting.

Location · Value · Pool

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, no kitchenette, 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.

Family · Location · Kitchen

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.

Value · Location · Hospitality