Southeast Massachusetts Luxury Holidays

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Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
  • 2 hours drive from Gillette Stadium
Stay at this 5-star luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (775 reviews)
"Old school hotel complex in a great location overlooking the Sea. Great ambience in the main lodge & dining facilities. Very kid friendly with the main pool swarming with kids. At one point I noticed 8 small kids in the large jacuzzi at one time - unusual for a luxury property. The pool experience ..."

Reviewed on 16 Jul 2025

Chatham Bars Inn
Candleberry Inn on Cape Cod

Candleberry Inn on Cape Cod

4.5 out of 5
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 WiFi, and free parking. Popular attractions Brewster Ladies' Library and Breakwater ...
10/10 Exceptional! (132 reviews)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."

Reviewed on 28 Jul 2025

Candleberry Inn on Cape Cod
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street, Brewster, MA
  • 2 hours drive from Gillette Stadium
Book a 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 our reviews. ...
8.2/10 Very Good! (999 reviews)
"Amazing stay and location!"

Reviewed on 24 Jul 2025

The Mansion at Ocean Edge
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.