Chilmark Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Wen C.

Top hotels in Chilmark

Sea Crest Beach Resort
Sea Crest Beach Resort
3.5 out of 5
350 Quaker Rd, North Falmouth, MA
The price is 6.999.304 ₫ per night from 25 Jun to 26 Jun
6.999.304 ₫
9.509.844 ₫ total
25 Jun - 26 Jun
includes taxes & fees
8.2/10 Very Good! (100 reviews)
"We go every year , it’s a beautiful place right on the ocean ."

Reviewed on 21 Jun 2025

Sea Crest Beach Resort
Summercamp
Summercamp
3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is 11.262.461 ₫ per night from 30 Jun to 1 Jul
11.262.461 ₫
12.580.169 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9.2/10 Wonderful! (998 reviews)
"I gave an overall rating of 4 because my room was so small, I was totally miserable. This Queen ocean view room, in the older part of the hotel is not worth the rate of over $550 per night. I regret not reserving a king room. I definitely will not make that mistake again. The property itself is an ..."

Reviewed on 22 Jun 2025

Summercamp
Vineyard Harbor Motel - Private Beach
Vineyard Harbor Motel - Private Beach
2.5 out of 5
60 Beach Road, Vineyard Haven, MA
The price is 9.348.365 ₫ per night from 7 Jul to 8 Jul
9.348.365 ₫
10.442.209 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (419 reviews)
"Friendly and clean"

Reviewed on 22 Jun 2025

Vineyard Harbor Motel - Private Beach
See all 2,293 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.

Frequently asked questions

How much does a Chilmark holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Chilmark costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chilmark?
January, February and November are great times to look for cheap Chilmark holiday packages. Choosing to travel in less busy months means you can usually find lower prices on accommodation and flights.
How many days is enough for Chilmark?
The ideal duration for your Chilmark holiday depends on what you'd like to do and see. Generally, a few days to a week will give you time to check out all the main sights and discover some hidden gems along the way.
Is it worth booking a holiday package to Chilmark?
Chilmark offers everything you need for an unforgettable trip. Begin your Chilmark holiday on a high note by visiting popular attractions like Lucy Vincent Beach.
How to find the best Chilmark package deals?
Landing a cheap Chilmark package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Chilmark package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Chilmark holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging stays and flights separately. Better still, you can personalise your Chilmark getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Chilmark?
If you've got your Chilmark travel dates finalized, book as early as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Chilmark?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Chilmark.
  2. Set a budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Chilmark. Then, pick a hotel that suits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Chilmark. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Chilmark holiday package that brings all your bookings together.

Popular places to visit

Chilmark Chocolates

Enjoy an outing to Chilmark Chocolates during your stay in Chilmark. While in this walkable area, you can savour the wineries.

Chilmark Chocolates

Fulling Mill Brook Preserve

Enjoy an outing to Fulling Mill Brook Preserve during your stay in Chilmark. Wander the area's waterfront or simply enjoy one of its wineries.

Fulling Mill Brook Preserve