Holiday rentals in Milk Island

Oceanfront Home Rockport

Step into your own slice of paradise with our newly renovated beachfront haven, perfectly perched along the captivating Long Beach in Rockport. Picture yourself waking up to the soothing sounds of waves and the mesmerizing sight of the ocean stretching out before you. With five cozy bedrooms accommodating up to 14 of your nearest and dearest, along with two sparkling bathrooms and a gleaming, fully equipped kitchen, this is the ultimate spot for unforgettable getaways with family and friends.

Luxury Portside Townhome Steps to Niles Beach

Escape to Niles Beach and experience the ultimate coastal getaway in our inviting 3 bedroom 3 1/2 bath townhome, just a short walk away from the serene Niles Beach in Gloucester. Perfectly situated for families, couples or friends looking to unwind by the sea. Explore Gloucester's historic harbor and waterfront, discover local seafood dining options and charming shops in downtown or take a scenic walk along Cape Ann's beautiful coastline. Book NOW and Experience the Magic of Gloucester!

The Crows Nest | Near Shops & Beaches

This charming New England style apartment, located on Main Street has lots to offer. Features include a full kitchen, living room, a bedroom with queen sized bed and soft décor, plus a fully private bathroom and plush towels. Enjoy the spacious living room filled with natural light. Includes a private entrance and wrap-around porch overlooking beautifully maintained grounds. Parking. A 10 minute walk to the Bearskin Neck, shops and beaches, and a 5 minute walk to the train station.

Waterfront Downtown Apartment • Walk Everywhere

Dreaming of a magical seaside getaway? Our charming eco-apartment in the Dream House awaits you! A beach lover's paradise, we're located directly on the ocean in the heart of downtown on Bearskin Neck. Watch the sunset from our amazing windows overlooking the harbor. Park the car and walk to shopping, dining, art galleries, Front Beach and Motif #1. Accessible by train and easy to get to from Boston and Salem. Make a trip to this charming New England seaside village a priority!

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, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

Lane's Cove Bijou

Kick back and relax by the cozy gas fireplace as you take in spectacular sunsets over the ocean. This calm, stylish space features a gourmet kitchen and a luxurious master bedroom suite that make this jewel of a house the perfect retreat for a couple. The spa-like master bath includes a large walk-in shower and a clawfoot tub with views of the cove. A second bedroom provides space for an additional guest. The dining table expands to comfortably seat eight for shared meals.

Stay at Front Beach

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Rare waterfront condo perched over Front Beach with harbor views ✓ Steps from Bearskin Neck, downtown Rockport, shops, galleries, and dining ✓ Bright classic coastal home with water views from nearly every room ✓ Private deck overlooking the beach, perfect for morning coffee or sunset drinks See more photos, video tours, and local recommendations on IG @staycapeann.

Sea Vagabond - Watch the waves, stroll to the sand

"The Sea Vagabond House is an expanded 1932 summer cottage, with spectacular views of the ocean waves, with the tidal Saratoga Creek offering a mesmerizing and changing scenes from inside and outside this charming vacation home. The home sleeps eight comfortably in beds. Each level offers a full bathroom with a bathtub/shower. There are plenty of bath towels and beach towels for each guest. "Comfortable, clean and close to the beach, we will return."

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.

Pleasant Place

Pleasant Place is a spacious, clean and centrally located spot to spend time with your family and friends. It has two bedrooms, two full bathrooms and a pull out couch. Sun soaked in natural light, it boasts a newly renovated kitchen, granite island, large dining room and a charming family room with views of the Rockport harbor. Walk downtown, to the beach, or drive around town and take advantage of your own parking spot in the busy summer.

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

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.