Holiday houses in Cape Ann

4.96 out of 5 average rating, 269 reviews

Guesthouse in Gloucester

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

4.89 out of 5 average rating, 223 reviews

Charming Rockport Studio Apt

10 min walk to Town, Bearskin Neck, Tuna Wharf & Rockport's world famous Motiff #1. Old Garden Beach 5 min walk. 15 min walk to Front Beach & Rockport Train Station (Rockport Line from Boston (North Station). Studio Apt has all amenities to cook yummy meals, cozy bed, wash clothes, WIFI, Cable TV in quiet peaceful neighborhood w/ off-street parking. Hardwood floors, high ceilings, lots of windows make this studio apartment an ideal launchpad from which to explore Rockport, Gloucester & Cape Ann.

4.99 out of 5 average rating, 268 reviews

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

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, 301 reviews

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! ⚓

4.98 out of 5 average rating, 102 reviews

1 Bedroom 1 Bath Waterview Downtown w/ Parking

Steps to ocean, steps to restaurants and shops. Quiet and quaint. Enjoy this centrally-located unit with all the town of Rockport has to offer right out the front door. Clean and fresh, with ocean views from the kitchen and living room. Unit has been renovated and updated with fresh paint, new appliances, new mattress and new sleeper sofa for guests. Enjoy the town shops, restaurants, sights, and beach all with a short scenic walk. This is Main Street, USA. Desirable Downtown Parking spot.

4.99 out of 5 average rating, 112 reviews

Guesthouse in Rockport

Gingerbread House | Steps to Beach| 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!

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

4.98 out of 5 average rating, 127 reviews

Guest suite in Rockport

Historic Rockport Large Suite, Entire Third Floor.

This 3rd floor suite is the entire top floor of a Historic home. Jack and Jill bathroom. Enjoy a short walk to Old Garden Beach , Front beach, Shalin Liu Performance Center and all of downtown shops, restaurants and art galleries. You will enter your suite via a keyless door up a private “good morning” staircase. Extra bedroom available- A second bedroom off of your private staircase on the second floor landing. Message for pricing. This is not included if no prior arrangement.

4.98 out of 5 average rating, 187 reviews

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!

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

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!

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Popular amenities for Cape Ann holiday rentals

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Free parking on premises

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Other great holiday rentals in Cape Ann

4.97 out of 5 average rating, 67 reviews

Gorgeous apartment, short walk to beach&downtown!

CourtneyRating, 5 stars3 weeks ago

This is a thoughtfully organized and stocked apartment in an adorable neighborhood, walkable to all of the Rockport sights and easy to find. I appreciated the adjustable desk, the amazingly easy to use tv, the Nespresso and the laundry. There were a lot of nice aesthetic details, too: real books, a lovely courtyard, pretty upholstery. Highly recommend.

Superhost

Cottage in Rockport

4.72 out of 5 average rating, 87 reviews

Quaint Oceanfront Cottage in Rockport MA

CindyRating, 5 stars9 months ago

Great little place for two! Sandy the neighbor was great along with her dog! 😊 great walking distance to shopping and restaurants! View is beautiful and breathtaking 😎will be back again in two years! Cindy and Gary from Ontario

4.97 out of 5 average rating, 34 reviews

Artistic studio with garden, walk to town/beaches

GlauciaRating, 5 stars1 week ago

This place is amazing! The outside is beautiful and the inside! I spent the weekend there with my daughter, and we walked everywhere! The small shops and restaurants were amazing. The host also provided lots of board games so we would play games when we got back. The studio is super cozy and lovely. I will book it again the next time we go back to Rockport!

5 out of 5 average rating, 242 reviews

Guesthouse in Rockport

Sea Mist Cottage Rockport, MA

DaveRating, 5 stars2 weeks ago

We’ve had the pleasure of renting John & Linda’s beautiful oceanfront cottage multiple times now—first for our engagement, then for the week after our wedding, and now for our anniversary and pregnancy announcement. This special place has become the backdrop for some of the most meaningful milestones in our lives. John & Linda are truly wonderful hosts—always providing excellent communication, thoughtful attention to detail, and a warm, welcoming atmosphere that makes the cottage feel like a home away from home. We’re so grateful for the memories we’ve made here, and we will absolutely be back!

Guest suite in Gloucester

5 out of 5 average rating, 33 reviews

The Artist Suite by Toi Moi

MeganRating, 5 stars1 day ago

What a lovely stay in such a lovely home. We truly enjoyed our stay and I would love to come back soon. The location was private and beautiful and so very peaceful. We attended a wedding in town and the location was close to so many restaurants and locations for the wedding it was a lovely space to recharge in between wedding events. I can't wait to come back and explore the hiking trails. Yewona & Gabriel were wonderful hosts and the space is more beautiful than the photos.

5 out of 5 average rating, 8 reviews

Home in Gloucester

Stay at Rocky Neck

KrisRating, 5 stars1 week ago

Great location and beautiful views. We will for sure look to stay here again on any future visits to Gloucester.

5 out of 5 average rating, 55 reviews

Panoramic Ocean Views in Rockport

ArianaRating, 5 stars3 days ago

Our stay at Jamila Casetta was absolutely wonderful! The location couldn’t be better—just a few minutes’ walk to all the shops and restaurants. The space was beautifully decorated, the bedding was super comfortable, and the kitchen had everything we needed. Communication with Christine was always smooth and helpful. We highly recommend this place and will definitely be back!