Luxury Hotels & Resorts in Chatham from NZ$222

Among the top-rated luxury hotels in Chatham, Massachusetts, Chatham Bars Inn, Captain's House Inn, and Chatham Wayside Inn are consistently celebrated for their exceptional quality.


The Chatham Bars Inn, with a 9.2 rating, is a distinguished resort offering a private beach and a range of amenities including tennis courts and massage services. Customers frequently praise its excellent service, helpful staff, and beautiful location.


The Captain's House Inn, rated 9.8, is renowned for its exceptional full breakfast and spacious, clean rooms. Guests consistently praise the friendly and helpful staff, highlighting the exceptional quality of the food.


The Chatham Wayside Inn, with a 9.2 rating, is ideally situated in a shopping district. It offers a complimentary continental breakfast and features a garden view restaurant. Reviewers often mention its charming, clean rooms, great location, and friendly staff.

The best area of Chatham for luxury hotels is along the waterfront near Main Street and Shore Road, offering direct access to the town's amenities and scenic views.


This central area is where you'll find the most upscale accommodation options. It's very walkable, with many hotels boasting views of the ocean or Oyster Pond. Main Street itself is lined with unique shops, art galleries, and acclaimed restaurants, all within easy reach. The Chatham Lighthouse is a prominent landmark just a short distance away, superb for a morning stroll.


Couples often find this area ideal for a sophisticated getaway. The proximity to fine dining, boutique shopping, and picturesque coastal walks creates a refined holiday experience. Many luxury hotels here offer high-end spa services and exquisite dining experiences on-site.


For those seeking a more secluded, yet still luxurious, experience, properties further along Shore Road towards North Beach Island provide exclusive access to private beaches and often come with expansive grounds.

For families seeking luxury accommodation in Chatham, the Chatham Wayside Inn and Chatham Bars Inn offer exceptional experiences.


The Chatham Wayside Inn, with a 9.2 rating, is known for its charming and clean rooms, as well as its excellent location within a shopping district. Reviewers frequently praise the friendly and extremely helpful staff, and the complimentary continental breakfast is a popular feature.


The Chatham Bars Inn, rated 9.2, is a resort-style property with a private beach. Its amenities are considered top, including on-site outdoor tennis facilities. Customers consistently highlight the excellent service and the beautiful, superb location.

Chatham offers several excellent luxury hotels with a pool, including Chatham Bars Inn, Chatham Wayside Inn, and Queen Anne Inn.


The Chatham Bars Inn, with a 9.2 rating, is an extensive resort offering a private beach and a range of amenities. Reviewers consistently praise the excellent service, helpful staff, and top amenities, including its pools.


The Chatham Wayside Inn, rated 9.2, is ideally situated in a shopping district. Guests frequently highlight the clean and charming rooms, the excellent location, and the clean pool. A complimentary breakfast is also available.


The Queen Anne Inn, with an 8.8 rating, provides a relaxing stay with its outdoor seasonal pool and sun loungers.

For couples seeking a luxury experience in Chatham, the Chatham Wayside Inn is an excellent choice.


The Chatham Wayside Inn, with a 9.2 rating, is particularly well-suited for a romantic getaway. It is located within a shopping district, offering convenience for guests. The hotel provides amenities such as bathrobes, champagne service, and designer toiletries, enhancing the luxury experience. Customers frequently praise the charming and clean rooms, the excellent location, and the friendly and extremely helpful staff. Complimentary continental breakfast is also available.

For luxury accommodation near Chatham Lighthouse Beach, the Chatham Wayside Inn is an excellent choice.


The Chatham Wayside Inn, with a 9.2 rating, is conveniently located within a shopping district and offers a range of premium amenities, including bathrobes, designer toiletries, and premium bedding. Guests frequently praise its charming, clean rooms and the friendly, extremely helpful staff. The hotel also provides complimentary Continental breakfast.

The best area to stay for luxury activities and experiences in Chatham is the area around Main Street and Shore Road, particularly close to the Chatham Bars Inn.


This central part of Chatham is the heart of the town, offering a refined blend of upscale amenities and classic New England charm. Main Street itself is lined with elegant boutiques, art galleries, and fine dining restaurants, all within easy walking distance. The Chatham Bars Inn, a prominent landmark, anchors the luxury experience here, boasting its own private beach and offering a range of high-end services.


Couples looking for a sophisticated getaway will find this area particularly appealing. You can enjoy strolls along Shore Road with views of the ocean, indulge in gourmet meals at top-rated restaurants, or explore the unique shops for local crafts and designer goods. Many luxury hotels here provide exclusive access to amenities like spa treatments, private boat charters, and bespoke culinary experiences.

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right luxury hotel in Chatham for you.

There are plenty of ways to save on a luxury hotel in Chatham. Join One Key™, our free travel rewards programme, to unlock Member Prices across a range of hotels. Typically, booking in advance will help you save on hotel bookings. If you're feeling spontaneous, be sure to check for last-minute deals.

Luxury hotel prices in Chatham vary, but you can find a great deal from NZ$222 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates.

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it’s wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.