Find your next unforgettable stay in Cape Ann.

A curated selection of stays designed for comfort, style, and an authentic Cape Ann experience. Whether you're drawn to the charm of Bearskin Neck or the soft sands of Good Harbor Beach, each property offers a seamless blend of thoughtful design and coastal living. Stay with us and experience Cape Ann on your terms.

Wooden deck with a dining table and wicker chairs overlooking a body of water with a buoy, an island with buildings, and a cityscape in the background under a partly cloudy sky.
Book a Stay
Book a Stay
  • A house built on a rocky shoreline with a deck and a floating dock extending into the water. The house has large windows, a sloped roof, and an outdoor staircase.

    Rocky Neck

    Set in the heart of America’s oldest art colony, Rocky Neck is a coastal retreat where creativity meets seaside charm. Wake up to harbor views, sip coffee on the deck, and spend your days wandering through galleries, waterfront cafés, and boutique shops. Whether you're soaking in the local culture or unwinding by the water, this artistic enclave is a destination like no other.

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  • A lakeside scene with a house on the left, a wooden dock extending into the water, lush green grassy area, and trees in the background under a blue sky with some clouds.

    Little River

    Nestled along the peaceful banks of Little River, this waterfront retreat is a perfect balance of nature and relaxation. Wake up to the sound of the tide, sip coffee on the dock, and spend your days kayaking through winding waterways or lounging by the water’s edge. Whether you're exploring nearby trails or soaking in the river views, this secluded haven is pure coastal charm.

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  • Aerial view of a residential neighborhood with lush green trees and several houses, including a gray house with a small deck and backyard, under clear blue sky.

    Good Harbor

    Steps from Gloucester’s most beloved beach, Good Harbor is the perfect blend of relaxation and adventure. Wake up to ocean breezes, sip coffee on the deck, and spend your days sinking your toes into soft white sand or exploring nearby coastal trails. Whether you're catching the sunrise over Salt Island or unwinding after a day in town, this seaside retreat is pure coastal bliss.

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  • Bright living room with white walls, sofa, and wicker chair, decorated with framed bird artworks, a white coffee table with flowers, and sliding glass door leading outside.

    Niles Beach

    Tucked away along Gloucester’s scenic coastline, Niles Beach is a serene retreat with sweeping harbor views. Wake up to the gentle sound of waves, sip coffee on the deck, and spend your days strolling the quiet shoreline or paddleboarding on calm waters. Whether you're watching sailboats drift by or exploring downtown’s vibrant scene, this hidden gem is pure coastal charm.

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A bedroom with a four-poster black metal bed frame, white bedding, and multiple brown and teal pillows. There are black wall sconces beside the bed, a wooden nightstand, a window with a bamboo blind, hardwood floor, and a beige area rug.

250+ ★ ★ ★ ★ ★ Star Ratings

250+ ★ ★ ★ ★ ★ Star Ratings

Stay with Confidence

Every Stay Collections home is thoughtfully designed and meticulously maintained, ensuring comfort, style, and a seamless experience from booking to checkout.

Live like a local.

Aerial view of a coastal area with a mix of lakes, residential houses, and green trees under a partly cloudy sky.

“The best travel memories come from the places you stumble upon, the meals you didn’t plan, and the moments that feel like they were meant just for you. We’re here to help you find them.”

Allie O’Brien
Customer Experience Lead

A woman with long brown hair, wearing a white sweater with blue horizontal stripes, sitting on a wooden bench on a porch with a wooden wall behind her, smiling and looking at the camera.

Get in Touch.

Ask a Question
Ask a Question

  • Email: inquiries@staycollections.com

    Phone: (978) 387-1573

  • Reach out, and we’ll help you find the perfect fit for your trip.

  • What amenities can I expect at your properties?

    Each property in our collection is thoughtfully curated with premium amenities, including high-quality linens, fully stocked kitchens, high-speed Wi-Fi, and smart TVs. Many of our properties also feature private outdoor spaces, waterfront access, or unique local touches for an exceptional stay.

    What is your cancellation policy?

    We understand that plans can change. If you cancel within 60 days of your stay, you will receive a 50% refund, and if you cancel within 30 days, your stay is non-refundable. Unlike a hotel, we don’t have interchangeable rooms, so when you book with us, we hold that specific home just for you. If you have any questions or need assistance with your reservation, feel free to reach out—we’re happy to help.

    What should I do if I need assistance during my stay?

    We provide 24/7 guest support to ensure your stay is seamless. Whether it’s a maintenance issue or a local recommendation, our team is just a call or message away to assist you.