Top Luxury Southeast Massachusetts Hotels

Chatham Bars Inn

297 Shore Rd, Chatham, MA

2 hours drive from Gillette Stadium

Stay at this 5-star luxury resort in Chatham. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the property condition ...

9/10 Wonderful! (791 reviews)

Excellent experience all around Gorgeous location and beautiful hotel Lively lobby

Reviewed on 13 Oct 2025

Candleberry Inn on Cape Cod

1882 Main St, Brewster, MA

2 hours drive from Gillette Stadium

Stay at this 4.5-star luxury B&B in Brewster. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Breakwater Beach and Rail Trail Bike Shop ...

10/10 Exceptional! (139 reviews)

Thank you for a great stay!

Charlene and Eric were amazing hosts! The breakfast is to die for. If they have blueberry pancakes on the menu during your stay, they are a must try!

Reviewed on 29 Aug 2025

The Mansion at Ocean Edge

2907 Main Street, Brewster, MA

2 hours drive from Gillette Stadium

Stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...

8.2/10 Very Good! (1,000 reviews)

Highly recommend. From check in to check out, the service was friendly, responsive and courteous. The room was also a great surprise. Large room with a large bathroom.Well appointed with a nice balcony. Good bathroom lighting for make-up and easy for two people to get ready at the same time. Beds ...

Reviewed on 22 Sept 2025

See all 11,054 properties in Southeast Massachusetts

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.