
When you’re vacationing with a larger group, having plenty of space is essential. Choosing accommodations that keep everyone together makes it easier to enjoy shared meals, relax in one place, and spend quality time without feeling crowded. Having separate rooms or scattered lodging can quickly become inconvenient and limit opportunities to gather as a group.
For this reason, vacation rentals that accommodate large groups are in high demand. If you’re interested in staying under one roof, we have variety of vacation homes that can accommodate larger groups. Consider our larger vacation homes or search our hand selected vacation rentals below that pair well together. Many of our ‘regular’ sized homes are very close to each other and can be booked together, keeping everyone side-by-side or within a short walking distance.
Stay Close Together on Cape Ann
Whether you’re looking for a historic retreat or a cozy waterfront escape, we’ve selected properties that pair perfectly together for your group vacation on Boston’s North Shore. Booking both homes provides the ideal combination of comfort, privacy, and unforgettable views while giving your group plenty of space to relax. With a total of seven bedrooms, you’ll enjoy the convenience of staying close together while taking advantage of easy access to Cape Ann’s scenic coastline, charming shops, and local attractions. Reserve your stay today and make the most of your getaway.

Check both Annisquam Singing Pines availability and Thurston Point Cottage and book both today! Annisquam Singing Pines offers five spacious bedrooms, making it an ideal choice for larger families or groups, while nearby Thurston Point Cottage features three comfortable bedrooms in a charming riverfront setting.
Check both Garden by the Sea availability and Seaside House and book both today! Garden by the Sea offers two comfortable bedrooms with beautiful views near Good Harbor Beach, making it the perfect retreat for a small family or couple, while Seaside House features four spacious bedrooms just steps from the sand, providing plenty of room for larger groups.


Check both Granite Cottage availability and Granite Pier and book both today! Granite Cottage offers a cozy one bedroom retreat with stunning views overlooking Granite Pier, making it perfect for couples or small families, while neighboring Granite Pier features three spacious bedrooms and plenty of room for larger groups.
Check both Sunrise on the Cove availability and The Rockporter and book both today! Sunrise on the Cove offers a peaceful waterfront retreat with three comfortable bedrooms, while The Rockporter features four spacious bedrooms in the heart of Rockport.


Need Even More Space? Give Us A Call!
Booking larger homes can be complex. Call us for assistance! Our guest experience specialist are here to help you plan your next getaway. Many of our homes are very close to each other and can be booked together, keeping everyone side-by-side or within a short walking distance.
To find the vacation home that’s right for your group, call our Guest Experience Specialists at (978) 290-4331 or book online.
