Chatham Vacations 2026 from CA $1,151

Chatham flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Eurostars The Boxer

West End

CA $1,151

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.

Boston Harbor Hotel

North End

CA $1,568

per person

Apr 21 - Apr 24

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.

The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,575

per person

Jun 13 - Jun 17

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.

Raffles Boston

Back Bay

CA $3,496

per person

May 25 - May 30

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

The Whitney Hotel

Beacon Hill

CA $2,400

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and TD Garden are located nearby.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd Chatham MA

CA $505

CA $578 total

Mar 25 - Mar 26

includes taxes & fees

Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Mayo House are located nearby.

On private beach

Pool

Chatham Wayside Inn

512 Main St Chatham MA

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Book a stay at this golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mayo House and Gallery Antonia are located nearby.

Pool

Breakfast included

Captain's House Inn

369 Old Harbor Road Chatham MA

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Stay at this B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Shark Center and Chatham Seaside Links are located nearby.

Breakfast included

Parking included

Surfside Inn Chatham

25 Holway St Chatham MA

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Book a stay at this beach B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Lighthouse and Chatham Windmill are located nearby.

Breakfast included

Parking included

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham MA

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Book a stay at this family-friendly vacation home in Chatham. Enjoy free WiFi, private pools, and a garden. Popular attractions Mayo House and Gallery Antonia are located nearby.

Pool

Hot tub

Chatham Seafarer Inn

2079 Main St Chatham MA

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Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cockle Cove Beach and Ridgevale Beach are located nearby.

Pool

Parking included

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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.

Popular places to visit

Chatham Lighthouse

Learn about the local history of Chatham when you spend time at Chatham Lighthouse. Wander the beautiful beaches and seaside in this trendy area.

Chatham Fish Pier

After visiting Chatham Fish Pier, make a plan to see the other sights and activities in Chatham. Wander the beautiful beaches and seaside in the area.

Historic Wind Mill at Chatham, Cape Cod Harbor

Chatham Windmill

Chatham Windmill is just one of the places to see in Chatham, so why not enjoy the other things to explore during your travels? Stroll along the seaside in this trendy area, or check out its seafood restaurants.

Chatham Vacations

If you're vacationing in Chatham and you don't know a lot about it, there's no need to stress — we can give you a hand!

To help get you oriented, Chatham is 75 miles (121 kilometers) to the southeast of the well-known city of Boston.

This part of Cape Cod boasts a population of around 1,000 people, some of whom will surely be willing to offer you some exciting travel tips.

Places to visit in Chatham

For many years, Chatham Lighthouse has reliably shown lost vessels the way through the storm. Head over to this proud tower and learn its stories. Want some more options? Kite flying by the seaside is something the whole family can get involved in. If it's a windy day, why not try to launch one at Cockle Cove Beach? And that's not all. Drop by Hardings Lighthouse, an endearing tower whose beam has led vessels through howling winds and crashing waves for years on end.

Where do you fly into for Chatham?

Get ready for some unforgettable experiences in Chatham. Once you've wandered out of Barnstable Municipal Airport (HYA), the center of town will be 17 miles (27 kilometers) away.

Frequently asked questions

How much are vacation packages to Chatham?

You can pick up a fantastic hotel and flight bundle for as low as CA $1,151. With a Travelocity vacation package, a trip to Chatham has never looked more enticing! Save both time and money and then get a start on packing those bags.

How long should my Chatham vacation be?

There are no rules for how long your Chatham vacation should be, but many travelers decide to stay around 3 nights. Got some wiggle room in your departure date? Consider booking a few more nights. Then you'll have enough time to check out the area's hidden treasures as well.

Where can I get the best vacation package deals for Chatham?

It's simple — browse Travelocity. With no less than 400 airlines and 1,000,000 properties worldwide, it's a piece of cake to craft a Chatham package deal that suits your travel style.

Why should I purchase my Chatham vacation package via Travelocity?

We have destinations and experiences for every type of globetrotter, top-quality service and 24/7 support. In addition to that, we'll match any better price you happen to find with our Price Match Guarantee.

Will I save money on my Chatham car rental if I combine it with hotels and flights?

You sure can — combine your hotel, car and flight into a Chatham vacation package and you can save a tidy sum. With so many things to do in and around Chatham, that set of wheels will make exploring a joy. Once you're behind the wheel, get out on the wide open road and make tracks to Fenway Park, an unmissable sight approximately 121 kilometers from Chatham.

Which airport is best for Chatham?

Martha's Vineyard Airport (MVY) is a major hub. You'll find it approximately 64 kilometers southwest of Chatham. Your other options are Nantucket Memorial Airport (ACK) (48 kilometers away from central Chatham) and Provincetown Municipal Airport (PVC) (48 kilometers away from central Chatham).

What is there to do in Chatham?

While taking the path less traveled is rewarding, you shouldn't ignore the big-name attractions that make a destination famous. Monomoy National Wildlife Refuge and Veterans Field are a couple of them in Chatham.

Where should I stay when visiting Chatham?

If you're after a place to base yourself, check out the Chatham Wayside Inn. It's the top choice for many travelers.