Holiday rentals in North Shore

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Top-rated holiday rentals in North Shore

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Top guest favourite

French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guest house in Annisquam

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

4.97 out of 5 average rating, 319 reviews

Top guest favourite

Flat in Rockport

4 Bed Water View w/ Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

4.99 out of 5 average rating, 175 reviews

Top guest favourite

A three-story blue house is framed by well-manicured greenery, including shrubs and small trees. A stone pathway leads to a welcoming front door, flanked by two rocking chairs. A balcony above adds architectural interest, and large windows allow for natural light.

Flat in Gloucester

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.

4.99 out of 5 average rating, 89 reviews

Top guest favourite

The contemporary tree house stands prominently against a clear blue sky, featuring expansive floor-to-ceiling windows that invite natural light. A vibrant blue staircase leads to the entrance. Lush greenery and carefully arranged landscaping enhance the modern design, creating a harmonious connection with nature.

Villa in Manchester-by-the-Sea

Secluded 20 Acre 10BR ultra contemporary Retreat

Family gatherings and family reunions. Make those family memories at this ultra contemporary take on a tree house. Original design based off the iconic Farnsworth house, updated with 10 Bed rooms of individual climate control atop of 20 acres of wildlife. Designer kitchen for the professional chef. Privacy that most movie stars long for. 5 min to beaches 10 min to Gloucester 20 min to historic Salem 45 min to Boston. Pesticide free landscaping Great location for family gatherings and reunions

4.97 out of 5 average rating, 75 reviews

Guest favourite

A spacious bedroom features a four-poster bed with soft linens and an inviting throw, complemented by warm yellow walls. Two bedside lamps cast gentle light beside the bed, while a plush ottoman and a patterned area rug provide additional comfort. A fireplace and framed artwork add to the room's charm.

Guest suite in Newbury

Parker River House Two Bedroom

This is a private two bedroom one bathroom second floor suite in the owner occupied Tudor style Parker River House. Minutes from downtown Newburyport, the train to Boston, The Governor’s Academy and many outdoor recreational opportunities, the unit overlooks the Parker River and the Great Marsh. It offers a seasonal sleeping porch, a luxurious marble bathroom, large outside deck with a dining table, in unit laundry, refrigerator, microwave and Keurig. Private entrance and adjacent parking.

4.97 out of 5 average rating, 103 reviews

Guest favourite

An expansive view of the ocean showcases rolling waves under a partially cloudy sky. A deck is visible, outfitted with outdoor seating, surrounded by lush greenery and coastal vegetation, creating a serene outdoor space.

Flat in Gloucester

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.

4.86 out of 5 average rating, 138 reviews

Top guest favourite

A framed artwork features the silhouette of a raven against a shimmering gold background. The ornate frame adds a touch of elegance, enhancing the gothic decor of the space.

Apartment in Salem

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

4.96 out of 5 average rating, 124 reviews

Guest favourite

Flat in Salem

Luxury Salem 2BR Apartment | Pool • Gym • Parking

Welcome to your perfect Salem getaway! Enjoy the comforts of home paired with upscale amenities for a truly unforgettable stay Highlights: • Close to Downtown Salem and the MBTA Commuter Rail • Meticulously deep-cleaned before every stay • Quartz countertops, stainless steel appliances and in-unit washer & dryer • Heated seasonal pool, rooftop terrace, fitness center. • Guest lounge, outdoor grills and modern co-working spaces • Walk to shopping, dining and the Salem Ferry to Boston

4.92 out of 5 average rating, 36 reviews

Top guest favourite

Flat in Rockport

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.

4.99 out of 5 average rating, 93 reviews

Top guest favourite

An open-concept studio showcases high ceilings featuring wooden beams and skylights that allow natural light to fill the space. A cozy seating area with two white chairs faces a large screen. A sleek kitchen bar with tall chairs is also visible in this inviting environment.

Place to stay in Beverly

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!

5.0 out of 5 average rating, 48 reviews

Top guest favourite

The living area is illuminated by natural light through the glass doors, showcasing a leather couch and a wooden coffee table. A chair and a modest decorative plant enhance the space, while sheer curtains softly diffuse the sunlight.

Flat in Essex

R. Hill Tree Top Studio!

Minutes from the coast along a wooded road, this property greets you with nature and art. With a tree top view filtering amazing sunsets you feel away from it all. This property is a place to create. Home of a metal sculptor, art is woven into a lifestyle of art and nature. The nearby studio is an amazing place that welcomes visitors. Wake to the wonderful trees and landscape this property has, while staying in our newly renovated, thoughtfully designed & styled space.

5.0 out of 5 average rating, 85 reviews

Top guest favourite

The exterior of the apartment is framed by lush greenery, showcasing a well-maintained lawn. A winding pathway leads to a red door framed by a white porch. Surrounding flowers add color amidst the soft shade of nearby trees, creating a serene atmosphere.

Flat in Beverly

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.

4.94 out of 5 average rating, 741 reviews