Luxury Holidays in Southeast Massachusetts 2026

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Chatham Bars Inn

297 Shore Rd Chatham MA

2 hours drive from Gillette Stadium

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

Candleberry Inn on Cape Cod

1882 Main St Brewster MA

2 hours drive from Gillette Stadium

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

10/10 Exceptional! (147 reviews)

"Amazing spot! The caretakers could not be better or nicer or now our friends! Beautiful and very comfy accomodations! A most delicious , and generous breakfast daily. Ice, coffee , tea a fridge all there for the taking. A most fabulous stay ! THANKS"

Reviewed on 31 Aug 2026

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! (1,002 reviews)

"Location, grounds and amenities were great for the Cape. Beautiful beach. Beautiful hotel. Beautiful grounds. The staff at the beach were nice and helpful. But check-in staff were incredibly rude to basically everyone who I saw there - our room still wasnt ready by 4pm check-in and they made it my ..."

Reviewed on 31 Aug 2026

See all 11,451 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.