South Chatham Vacation Packages 2026 from $1,008

South Chatham flight + hotel vacation packages

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

The Highliner Hotel

Downtown Gloucester

Save 100% on your flight

$1,008

per person

Jun 8 - Jun 12

found 23 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Boston (BOS)

This hotel features free WiFi in public areas, express check-out, and concierge services. A virtual front desk are provided for your convenience.

The Ritz-Carlton, Boston

Downtown Boston

Save 100% on your flight

$1,155

per person

Jun 18 - Jun 20

found 20 hours ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Limo/town car service, a lobby fireplace, and a hair salon are also on offer.

Hilton Boston Park Plaza

Bay Village

Save 100% on your flight

$1,299

per person

Jun 17 - Jun 22

found 23 hours ago

Roundtrip flight included

Houston (IAH) to Boston (BOS)

This luxury hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a 24-hour business center, and a coffee shop are also offered.

Lighthouse Inn

Save 100% on your flight

$1,040

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Boston (BOS)

A private beach and an outdoor tennis court are featured at this smoke-free hotel. Spend a day at the beach windsurfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with mini golf and a playground, and families will appreciate the onsite laundry facilities.

Summer House Hotel

Save 100% on your flight

$1,442

per person

Jun 20 - Jun 23

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Boston (BOS)

This hotel features a private beach and 2 restaurants. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas. Enjoy the seasonal outdoor pool and unwind at the beach bar and poolside bar.

Top South Chatham hotels deals

Chatham Tides

394 Pleasant St South Chatham MA

$179 nightly

$205 total

Apr 30 - May 1

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and a computer station are also on offer.

Parking included

Free WiFi

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$202 total

May 3 - May 4

Total with taxes and fees

This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Pool

Hot Tub

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$138 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features 2 poolside bars, 2 bars/lounges, and an indoor pool. Enjoy the gym and free perks like buffet breakfast and free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Hot Tub

Aiden by Best Western Cape Cod - West Yarmouth

476 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the 24-hour gym and perks like free self parking.

Pool

Breakfast included

Chatham Bars Inn

297 Shore Rd Chatham MA

$376 nightly

$430 total

Apr 19 - Apr 20

Total with taxes and fees

A private beach, a full-service spa, and 3 outdoor tennis courts are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free valet parking and a free beach shuttle.

On private beach

Pool

Chatham Wayside Inn

512 Main St Chatham MA

$190 nightly

$218 total

May 14 - May 15

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Pool

Breakfast 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

Forest Beach

Why not spend a lazy afternoon at Forest Beach during your trip to South Chatham? While you're in the area, stroll along the beaches.

Chatham Chamber of Commerce

After visiting Chatham Chamber of Commerce, make a plan to see the other sights and activities in South Chatham. Wander the beautiful beaches and seaside in this family-friendly area.

Frequently asked questions

How much are vacation packages to South Chatham?

Adventure calls in South Chatham, with Travelocity vacation packages from as low as $1,008. Providing both flights and hotels, these terrific deals are an easy way to explore more of our wonderful planet.

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

Travelocity has everything you need to score an awesome South Chatham package deal. Choose from as many as 400 air carriers and 1,000,000 properties worldwide and put together a vacation package that suits your style. With almost endless choice, it's easy to plan your next big adventure.

Why should I purchase my South Chatham vacation package via Travelocity?

Travel is all about making cherished memories and leaving all your troubles behind — which is why we have a professional team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our huge range of destinations. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.

Can I save money on my South Chatham car rental if I book it with a hotel or flight?

Most definitely — and booking one of our South Chatham vacation packages is the simplest way to go about this. Bundle any combination of a hotel, flight, car and tour and enjoy terrific discounts. The more you book, the more you save. There are loads of famous sights around South Chatham that are worth a road trip, including Fenway Park (70 mi from South Chatham). Nothing beats exploring places like this with the freedom of your own set of wheels.

What is there to do in South Chatham?

As you're ambling around South Chatham, be sure to drop by Forest Beach and Chatham Chamber of Commerce. Don't worry, you won't be bored here!