Holiday rentals in Cape Ann

Guest house in Gloucester

4.96 out of 5 average rating, 270 reviews

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, 225 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, 187 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, 302 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! ⚓

4.86 out of 5 average rating, 120 reviews

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.

4.9 out of 5 average rating, 199 reviews

Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2025! 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

Apartment in Rockport

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!

4.95 out of 5 average rating, 111 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!

4.98 out of 5 average rating, 690 reviews

Guest suite in Rockport

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.

4.87 out of 5 average rating, 214 reviews

Guest suite in Rockport

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Cape Ann holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cape Ann

5 out of 5 average rating, 38 reviews

Home in Rockport

Eden Cove

KimRating, 5 stars2 months ago

The views this home offers are beautiful. It is a nice neighborhood for walking a dog. The home has everything you would need. The host is very responsive.

5 out of 5 average rating, 30 reviews

The Crow’s Nest – Loft with Stunning Ocean Views!

TammyRating, 5 stars2 weeks ago

I stayed here a few nights and this Airbnb's location on Bearskin Neck was ideal for exploring Rockport. It's close to Bean and Leaf Cafe for a caffeine fix, many charming shops, multiple restaurants and Cape Hedge. I appreciated the ocean views from the living room. Since it's on the third floor, you feel removed from the tourist crowd while being close to everything. It's spacious with a comfortable couch and beds. It had a lot of storage too. The bedroom area is over another Airbnb and at night, I could hear the conversation clearly of those staying on the lower floor. Noise wasn't an issue elsewhere in the unit. Overall, I had a lovely stay. I highly recommend Fleur Cuisine for lunch or dinner. It was incredible.

Guest suite in Gloucester

5 out of 5 average rating, 34 reviews

The Artist Suite by Toi Moi

MeganRating, 5 stars6 days 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, 29 reviews

Treehouse By-the-Sea

MarianneRating, 5 stars1 week ago

our stay here was lovely. ellen and rusty were waiting for us when we arrived and helped us park. the space itself is cozy and clean. a treehouse indeed, up a bunch of stairs and surrounded by lovely oaks! ellen was an excellent communicator. she was flexible with our checkout as no one was following us and our first day was totally rained out. the location is lovely; a nearby beach and just under a mile walk to downtown. would recommend!

5 out of 5 average rating, 57 reviews

Apartment in Rockport

Panoramic Ocean Views in Rockport

SavannahRating, 5 stars3 days ago

This was one of our best Airbnb experiences. Every detail was thought of. The home was meticulously clean and welcoming. Location was perfect. Christine and Greg were kind and helpful. We are so grateful!

Holiday home in Gloucester

4.98 out of 5 average rating, 57 reviews

On the Water Gem - 2 BR -The Cove Lanesville

NathanRating, 5 stars7 months ago

Beautiful house and property, high quality and clean interior. Host responds fast and was flexible, easy to work with and very friendly.

Superhost

Guest house in Gloucester

4.91 out of 5 average rating, 93 reviews

Plum Cove Cottage with king suite!

MilesRating, 5 stars1 month ago

I spent 3 weeks at Christine’s fabulous cottage while working in the area. I felt a pang of sadness as I closed the door for the last time…this comfortable, charming little retreat had become home! It is airy and bright, the full kitchen is well-appointed and functional, the bathroom is clean and well-designed, and the sleeping loft is cozy and breezy at the same time! Christine is a responsive and pleasant host, check-in is easy. I will be back!