Photo by Wen C.

Find 5 Star Hotels in Chilmark, MA from $395

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare Chilmark 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Shower, designer toiletries, hair dryer, bathrobes
Harbor View Hotel
5.0 star property
8.8 out of 10, Excellent, (942)
"We had a beautiful room in the old house with amazing views over the ocean. Very special."
The price is $395
$455 total
includes taxes & fees
May 1 - May 2
Harbor View Hotel

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chilmark.
Vineyard Square Hotel & Suites

Vineyard Square Hotel & Suites

38 North Water Street, Edgartown, MA
Get rates
9/10 Wonderful! (222 reviews)
Still don't see what you're looking for?
See all properties in Chilmark.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Ready for an incredible adventure? Add further enjoyment on your next trip to Chilmark by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Chilmark so popular in the last year. There's no reason to delay a getaway to Chilmark any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Chilmark are the perfect places to relax in during your next escape. You deserve an outstanding getaway.

Get a Great Deal on 5-Star Hotels in Chilmark

You'll have a fantastic time at one of these 5-star hotels. High-end restaurants, concierges, and in-room spa sessions are all at the ready. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready to kick back and indulge. How do you want to relax? A concierge to help you make reservations at that outstanding restaurant? A full-body massage to help your cares fall away? Fluffy down pillows, lip-smacking main courses, and even spectacular views...these hotels have it all. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

But you aren't going to spend your entire vacation in your room, of course. We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Chilmark are waiting for you to rest up after a busy day.

Make Your Escape

The results are in, and Chilmark 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Decide on one of our Chilmark 5-star hotels today and soothe yourself in luxe surroundings tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chilmark?
You’ll find several pricing options for a 5-star hotel in Chilmark on Expedia. The amount you pay will depend on when you travel, trip length and other factors. Compare available properties for your desired dates and use our pricing and other filters to lock in the perfect upscale stay.

  • Search for the lowest price per night from $395

What makes a hotel 5 stars in Chilmark?
Flawless guest service is the defining feature of every 5-star hotel in Chilmark. From the second you arrive, staff attend to your every need, whether answering room service calls 24/7 or providing a turn-down service. Also, hotels have to offer top-rate conveniences to qualify for a 5-star rating. These can include luxury bathrobes, on-site spa facilities, swimming pools, fine dining restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chilmark?
Our filters are the easiest way to find exactly what you want. Select “All inclusive” and “5-star” to show the most luxurious properties in Chilmark where your meals, accommodations, entertainment and activities are included in the price. At these stays, your vacation is pure indulgence from the moment you arrive.
Are there any 5-star vacation rentals in Chilmark?
Although there aren’t any 5-star vacation rentals in Chilmark on our site, we have a range of stays that promise a memorable getaway. Discover one that suits your needs by searching our vacation rentals in Chilmark.

Recent reviews of Chilmark hotels
Expedia verified reviews

Harbor View Hotel

Harbor View Hotel

5/5 Excellent
Great location; beautiful views. Peaceful retreat
"We had a beautiful room in the old house with amazing views over the ocean. Very special."
A verified traveler stayed at Harbor View Hotel
Posted 11 days ago
Harbor View Hotel