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! (149 reviews)

"Exceeded expectations lots of small details and thoughtful extras for their guest."

Reviewed on 13 Sept 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! (1,006 reviews)

"The room was dirty, the tub has two holes, light switches broken. Wallpaper coming off the walls, bed had stains and the indoor pool had bugs and mold everywhere. The shower walls had black mold. The staff was not helpful at all. Carpet was not vacuumed."

Reviewed on 25 Sept 2026

See all 11,320 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.