South Dennis Vacation Packages 2025/2026 from $259

South Dennis flight + hotel vacation packages

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

Best Western Springfield West Inn

$259

per person

Nov 7 - Nov 9

found 9 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$382

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Beacon Hill Hotel

Beacon Hill

Save 100% on your flight

$547

per person

Nov 18 - Nov 21

found 16 hours ago

Roundtrip flight included

Cleveland (CLE) to Boston (BOS)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free continental breakfast is served.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,053

per person

Dec 15 - Dec 18

found 15 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Raffles Boston

Back Bay

Save 100% on your flight

$1,074

per person

Dec 11 - Dec 14

found 12 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Top South Dennis hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$203 total

Oct 26 - Oct 27

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

Cape Sands Inn

149 Main St - RT 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Oct 7 - Oct 8

Total with taxes and fees

This motel features an indoor pool and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the hot tub and perks like free self parking and free WiFi.

Pool

Hot Tub

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Pool

Breakfast included

Hyannis Harbor Hotel

213 Ocean St, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$173 total

Nov 4 - Nov 5

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.

Pool

Free WiFi

Hyannis Travel Inn

18 North St, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$113 total

Oct 7 - Oct 8

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and express check-out are also on offer.

Pool

Hot Tub

Hyannis Inn

473 MAIN ST, Hyannis, MA

Get rates

An indoor pool, free self parking, and concierge services are featured at this motel. WiFi in public areas is free. A terrace, a garden, and express check-out are also on offer.

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

Cape Cod Rail Trail

Enjoy a trip to Cape Cod Rail Trail and popular activities like golfing in South Dennis. Wander the beautiful beaches and waterfront in this family-friendly area.

Frequently asked questions

How much are vacation packages to South Dennis?

You can land an amazing flight and hotel bundle for as low as $259. With a Travelocity vacation package, a stay in South Dennis has never been more tempting! Save both time and cash and then get a head start on packing those bags.

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

Walking away with the best package deal to South Dennis is a cinch with Travelocity. With around 400 partner airlines and 1,000,000 properties around the world, you'll have loads of choice when it comes to picking your flights and hotels.

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

Nothing beats the peace of mind knowing you've just bagged the best deal available — that's our Price Match Guarantee. Add to that our impressive range of destinations and 24/7 team of customer service professionals and you've got the formula for a hassle-free vacation.

Can I save money on my South Dennis car rental if I combine it with my hotel or flight?

Certainly — bundle your car, flight and hotel into a South Dennis vacation package and you can save a handsome sum. With so much to discover in and around South Dennis, having your own wheels will more than come in handy. Once you're behind the wheel, hit the wide open road and head toward Fenway Park, a well-known sight about 65 mi from South Dennis.

Which airport is best for South Dennis?

Martha's Vineyard Airport (MVY), located around 35 mi southwest of downtown South Dennis, is most likely where you'll touch down. Your other choices are Nantucket Memorial Airport (ACK) (30 mi away from central South Dennis) and Provincetown Municipal Airport (PVC) (25 mi away from central South Dennis).

What is there to do in South Dennis?

Cape Cod Rail Trail is just one of the superb sights that make South Dennis such a tourist hot spot. But give yourself enough time to roam the city's lesser-known attractions too. This is sometimes where the best memories are made.

Where should I stay when visiting South Dennis?

If you're searching for a place to lay your head, check out the Sesuit Harbor House. It's the top choice for many visitors.