Book Exclusive Chatham Vacation Packages

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Chatham flight + hotel packages

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

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,807, price is now CA $1,151 per person
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

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,808, price is now CA $1,568 per person
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

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,462, price is now CA $1,575 per person
CA $1,575
per person
Jun 13 - Jun 17
found 12 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

Raffles Boston

5 out of 5
Back Bay
Price was CA $5,401, price is now CA $3,496 per person
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

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $3,612, price is now CA $2,400 per person
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

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $505 per night
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

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Get rates
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

Captain's House Inn

4 out of 5
369 Old Harbor Road Chatham MA
Get rates
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

Surfside Inn Chatham

2.5 out of 5
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!

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

Chatham MA
The price is CA $2,333 per night
CA $2,333
CA $3,892 total
Apr 10 - Apr 11
includes taxes & fees
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

Chatham Seafarer Inn

3.5 out of 5
2079 Main St Chatham MA
Get rates
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

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 Lighthouse
Chatham, Cape Cod Fish Pier and Harbor

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.

Chatham Fish Pier
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 Windmill

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.

Photos of local treasures

Browse Chatham vacation photos for more inspiration

Chatham showing a house and boating
Chatham featuring a windmill, general coastal views and wild flowers
Chatham showing a house and a sandy beach as well as a small group of people
Chatham showing boating
Chatham showing a lighthouse