Holiday houses in Milk Island

4.96 out of 5 average rating, 136 reviews

Harborside Oasis | Harbor View | Heart of Downtown

Step into Coastal Bliss at Our Rockport Apartment! 🌊🏠 Perfectly positioned just steps from Bearskin Neck, immerse yourself in unique shops 🛍️, exquisite dining 🍽️, and serene beaches 🏖️. Revel in the spectacular views of iconic Motif Number 1 from your balcony, enjoy high-speed WiFi, and a 55" Smart TV in a fully stocked kitchen. Ideal for soaking in Rockport's vibrant yet relaxing atmosphere. Note: Requires climbing stairs and can get noisy! Book your unforgettable seaside retreat today! ⚓

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, 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.

4.99 out of 5 average rating, 114 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 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.

4.94 out of 5 average rating, 124 reviews

Guest suite in Rockport

The Perfect Get-Away Suite | Near Shops & Beaches

Everything in this suite is new, clean, tidy and modern. There is plenty of natural light and privacy blinds. There is Wifi and HD Cable with Netflix, Prime and other platforms. There is also a kitchenette in the unit with sink, small refrigerator, microwave oven and coffee maker. The house sits on a third acre of land and is fenced in from the road. We are a ten minute walk to the beach and shopping area, and the train station is located only two blocks away.

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, 110 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.

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Other great holiday rentals in Milk Island

Guest suite in Gloucester

5 out of 5 average rating, 46 reviews

Beachside~at Good Harbor Beach 2 person 1 bedroom.

SheaRating, 5 stars1 month ago

Lois’ place was conveniently located by the beach, restaurants, ice cream, and coffee. It was perfect for a nice walk on the beach in the morning. The place was clean, perfect size for two people with parking accommodations. We will surely be back!

Cottage in Rockport

4.79 out of 5 average rating, 110 reviews

Retreat in the Trees- walk to Cape Hedge Beach

ParkerRating, 5 stars7 months ago

This place truly gave "treehouse" vibes - with being up on a hill and with the big windows, it was a pleasure waking up here each morning to see all the trees with their autumn leaves. This is such a unique house - and it included all the amenities we needed. The location was also great and it was easy to get around and explore the area. 10/10 would stay here again!

4.95 out of 5 average rating, 55 reviews

Home in Rockport

Charming waterfront home. Patio, AC, Shops, Dining

LyndaRating, 5 stars2 weeks ago

I can’t thank you enough for letting me stay in this beautiful location. I’ve been going through chemo treatment and trying to find beautiful places in between treatment to enjoy. This place was a fav. Which I sort of want to keep to myself. I didn’t have a lot of energy to do a lot but it was exactly what I needed. Parked my car and left it behind. Watched the tide, walked around a beautiful place with my dog. I couldn’t ask for more.

5 out of 5 average rating, 6 reviews

Cottage in Rockport

sweet cottage by the sea

DavidRating, 5 stars8 months ago

I grew up in Rockport and when my wife and I needed to be in the area for a wedding, Shannon’s cottage was perfect for us. The views from the cottage and on walks near the cottage are spectacular.! The cottage had everything we needed and was very comfortable! Shannon is a great and responsive host and I highly recommend a stay at her cottage!!

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!

4.95 out of 5 average rating, 59 reviews

Apartment in Gloucester

New Design - Walk to DNTN, Beauport, Beach, Train

ChrisRating, 5 stars6 days ago

Perfect location to stay, and very clean and orderly. The host was responsive, and answered all our questions. I would definitely stay here again.

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!