Places to stay near Cape Ann Whale Watch

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Top-rated holiday rentals near Cape Ann Whale Watch

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A modern living area features a light-colored sofa adorned with decorative pillows and a natural wooden coffee table. A round mirror reflects light, while a small wooden side table and a potted plant add a touch of greenery. Soft ambient lighting enhances the soothing atmosphere.
Flat in Gloucester
4.97 out of 5 average rating, 145 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 its location for your visit.

Top guest favourite
The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.
Guest house in Rockport
4.99 out of 5 average rating, 152 reviews

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

Top guest favourite
A two-story white house rests on rocky terrain near the water’s edge. Large windows and a four-season porch are visible, allowing for scenic views. The structure is elevated on stilts, with greenery framing the property and a calm harbor in the background.
Home in Gloucester
4.93 out of 5 average rating, 178 reviews

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

Guest favourite
A bright living area features large windows allowing natural light to fill the space. A comfortable sofa and a cozy armchair sit on a patterned rug, with a wooden coffee table in between. A dining table is visible in the background, creating a welcoming atmosphere.
Flat in Gloucester
4.93 out of 5 average rating, 129 reviews

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

Top guest favourite
A charming log cabin is surrounded by lush greenery. Two miniature horses graze leisurely on the grass in front of the cabin, which features a covered porch and simple landscaping with flowers. Sunlight filters through the trees, highlighting the serene woodland setting.
Cabin in Rockport
4.97 out of 5 average rating, 489 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.

Top guest favourite
A panoramic view reveals the tranquil ocean, with soft waves lapping against the shore. Green trees and distant sandy areas are visible, enhancing the natural scenery. Several rooftops in the foreground provide a sense of elevation and perspective towards the coastline.
Home in Gloucester
4.98 out of 5 average rating, 103 reviews

Ocean views! Welcome to Sea Breeze! Winter rates!

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family.

Guest favourite
Apartment in Gloucester
4.95 out of 5 average rating, 139 reviews

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

Top guest favourite
An open living space features hardwood floors and a modern aesthetic. A sleek fireplace is mounted on the wall beneath a flat-screen TV. Bar stools with orange upholstery are positioned at the kitchen island, and a glass coffee table sits on a patterned area rug.
Apartment in Gloucester
4.98 out of 5 average rating, 125 reviews

Boho Beach Condo for Ocean Escape

Enjoy a stylish experience at our centrally-located oceanfront condo. We are walkable to exquisite beaches and parks as well as downtown Gloucester where you will find a number of bars and restaurants to explore. If you feel like hanging in, share a meal/cocktail on the private deck. Perfect for a couples getaway or a group of friends looking to explore the North Shore without ever getting in your car.

Top guest favourite
Cottage in Gloucester
4.97 out of 5 average rating, 149 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Now with mini-split A/C throughout and new windows in the bedrooms! Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Guest favourite
An open-concept living area is highlighted by a modern kitchen featuring a large island with seating for four. A spacious seating area with a blue couch complements the dining space, while a sliding door leads to an outdoor patio. Ample lighting enhances the contemporary design.
Flat in Gloucester
4.87 out of 5 average rating, 130 reviews

Long Beach Suites: Steps Away From Surf!

Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly built with summer visitors in mind. Long Beach Suites is just steps away from Long Beach in Rockport and only ten minutes to Good Harbor. You will be staying one of four similar apartments, photos may not be of exact unit.

Top guest favourite
A private outdoor deck is visible, featuring a round table and two chairs with aqua cushions. Scenic ocean views extend beyond the railing, framed by lush greenery and boats in the harbor. The serene setting invites relaxation and outdoor dining.
Holiday home in Rockport
4.96 out of 5 average rating, 110 reviews

Dreamy Oceanfront Stay For 2 • Heart of Downtown

Dreaming of a magical seaside getaway this summer? Our romantic eco-apartment in the Dream House awaits you! Located directly on the ocean in the heart of downtown. Watch the sunset every night from your private deck. Steps to shopping, dining and art galleries. We do our best to make it comfortable and enjoyable for you. We would love to host you for your Cape Ann visit!

Guest favourite
Guest suite in Gloucester
4.9 out of 5 average rating, 105 reviews

Welcoming, Quiet Gloucester Space

We look forward to welcoming you! From this downtown Gloucester apartment you'll have easy access to beautiful beaches, outstanding restaurants, museums, storied history, attractions, and adventure. America’s oldest seaport with an authentic working waterfront, and home to the oldest working art colony in America, Gloucester provides a one-of-a-kind destination experience.

Popular amenities for holiday rentals near Cape Ann Whale Watch