Southeast Massachusetts Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ₹43,962 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Luxury Southeast Massachusetts Hotels
Chatham Bars Inn
297 Shore Rd, Chatham, MA
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 ...
9.2/10 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
Candleberry Inn on Cape Cod
1882 Main St, Brewster, MA
Stay at this 4.5-star luxury B&B in Brewster. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Brewster Ladies' Library and Breakwater ...
10/10 Exceptional! (130 reviews)
"This is a beautiful property and Charlene and Eric are wonderful hosts. They are extremely attentive to a visitor’s needs and have delightful staff. The breakfast is excellent and has daily variations. My wife and I spent two nights at the Inn and would recommend it unreservedly."
Reviewed on 10 Jul 2025
The Mansion at Ocean Edge
2907 Main Street, Brewster, MA
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! (999 reviews)
"Every employee was friendly and helpful. The Beach Bar was wonderful, the Front Lawn fun, and the Ocean Terrace was delicious and beautiful. Our room #226 in the East Wing was clean, large, quiet and beautiful. The only negative was the price - with taxes and fees $725/night."
Reviewed on 16 Jul 2025
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.