Chatham Holidays

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Chatham Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Mansfield

Fairfield Inn & Suites by Marriott Mansfield

2.5 out of 5
Price was S$1,289, price is now S$994 per person
S$994
per person
22 Nov - 29 Nov
found 1 day ago
Return flight included
Charlotte (CLT) to Boston (BOS)
9.4/10 Exceptional! (648 reviews)
clean room, good staff!

Reviewed on 28 Sept, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was S$3,689, price is now S$2,580 per person
S$2,580
per person
22 Nov - 29 Nov
found 1 day ago
Return flight included
Charlotte (CLT) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!

Reviewed on 15 Sept, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Price was S$1,315, price is now S$1,001 per person
S$1,001
per person
22 Nov - 29 Nov
found 1 day ago
Return flight included
Charlotte (CLT) to Boston (BOS)
8/10 Very Good! (2,073 reviews)
Friendly staff at the front desk

Reviewed on 5 Oct, 2025

The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Price was S$1,684, price is now S$1,285 per person
S$1,285
per person
22 Nov - 29 Nov
found 1 day ago
Return flight included
Charlotte (CLT) to Boston (BOS)
8.4/10 Very Good! (1,943 reviews)
Staff is very hospitable without asking for additional help

Reviewed on 5 Oct, 2025

Holiday Inn Boston - Dedham Hotel & Conference Center by IHG

Holiday Inn Boston - Dedham Hotel & Conference Center by IHG

3 out of 5
Price was S$1,423, price is now S$1,095 per person
S$1,095
per person
22 Nov - 29 Nov
found 1 day ago
Return flight included
Charlotte (CLT) to Boston (BOS)
7.8/10 Good! (1,007 reviews)
Alright experience. Power outlets were not working, lights were flickering at times. AC was not working properly. Hallway had an odour.

Reviewed on 4 Oct, 2025

Chatham Beach Holiday

There's nothing that can beat a Chatham holiday. Whether you're indulging in fancy cocktails at a local hot spot or flipping through a book by the shore, your trip to Chatham is the perfect time to live out your beachy dreams. Many travellers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town centre. However, you'll also find a fantastic range of Chatham holiday packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Top hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is S$586 per night from 31 Oct to 1 Nov
S$586
31 Oct - 1 Nov
includes taxes & fees
9/10 Wonderful! (789 reviews)
"Beautiful property. Great service!"

Reviewed on 28 Sept, 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
9.2/10 Wonderful! (569 reviews)
"A really wonderful spot percolated to explore the cape. A very nice breakfast in the morning!"

Reviewed on 2 Oct, 2025

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Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
8.8/10 Excellent! (243 reviews)
"Clean room and well maintained buildings and pool area"

Reviewed on 24 Sept, 2025

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Greyfinch Chatham Inn
See all 4,954 properties in Chatham
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.