Chilmark Holidays

Photo by Wen C.

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Chilmark Beach Holiday

Whether you're travelling solo or with the whole gang, it'll be easy to find rest and relaxation on your Chilmark holiday. Search around for shiny rocks and shells or simply sit and watch the sunset. Whatever you choose to do, your trip to Chilmark will certainly be memorable. Lucy Vincent Beach, located 2 kilometres from the town centre, is perfect for those after convenience. Many visitors also lock in Chilmark holiday packages closer to Menemsha Beach, another great nearby option.

Top hotels in Chilmark

Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is S$181 per night from 13 Oct to 14 Oct
S$181
13 Oct - 14 Oct
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"Property clean. Husband walking issues. I told them. We got first floor, but it was down the end so we needed car to access lobby, pool. Continental Breakfast was just ok. Attached restaurant really good, but limited.No quick sandwich or burger type food. Attached lounge closed by 9, 10 friday and ..."

Reviewed on 14 Sept, 2025

Falmouth Inn
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd, North Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is S$221 per night from 19 Oct to 20 Oct
S$221
19 Oct - 20 Oct
includes taxes & fees
7.8/10 Good! (205 reviews)
"Beautiful beach. Perfect sand & sea. Buffet breakfast actually well maintaned until the very end. No running out of food. Clean rooms, courteous staff"

Reviewed on 15 Sept, 2025

Sea Crest Beach Resort
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 1 Oct to 2 Oct
S$149
1 Oct - 2 Oct
includes taxes & fees
8/10 Very Good! (97 reviews)
"The beds were so comfy, the staff was wonderful, and the restaurant was delicious!!"

Reviewed on 14 Sept, 2025

Iris Hotel Cape Cod
See all 2,219 properties in Chilmark
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.

What to do in Chilmark

All New Shared Jaws tour Budget Friendly

All New Shared Jaws tour Budget Friendly

S$168
per adult
All New Shared Jaws tour Budget Friendly
4 hours Hop-on Hop-off Jawsome Jaws Tour

4 hours Hop-on Hop-off Jawsome Jaws Tour

S$154
per adult
4 hours Hop-on Hop-off Jawsome Jaws Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

S$58
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
See all activities in Chilmark

* 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.