South Dennis Vacation Packages 2026 from $764

South Dennis flight + hotel vacation packages

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

Good Hotels Boston

South End

Save 100% on your flight

$764

per person

Aug 1 - Aug 5

found 22 hours ago

Roundtrip flight included

Charlotte (CLT) to Boston (BOS)

Express check-in, express check-out, and luggage storage are available at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Laundry facilities and a virtual front desk are also provided.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,334

per person

Aug 1 - Aug 5

found 22 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

Hyatt Regency Boston/Cambridge

MIT

Save 100% on your flight

$887

per person

Sep 13 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

By the Sea Guests Bed & Breakfast & Suites

Save 100% on your flight

$1,215

per person

Aug 12 - Aug 18

found 2 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Eurostars The Boxer

West End

Save 100% on your flight

$1,440

per person

Sep 13 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. A computer station, dry cleaning, and luggage storage are also on offer.

Top South Dennis hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$349 nightly

$399 total

Jul 5 - Jul 6

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.

Riviera Beach Resort

327 South Shore Drive South Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$429 nightly

$491 total

Jul 12 - Jul 13

Total with taxes and fees

A private beach and an indoor pool are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities.

Parker Beach Lodge

192 S Shore Dr South Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$186 total

Jun 29 - Jun 30

Total with taxes and fees

A seasonal outdoor pool, free self parking, and concierge services are featured at this hotel. WiFi in public areas is free. Express check-in, express check-out, and luggage storage are also on offer.

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$256 nightly

$293 total

Jun 29 - Jun 30

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.

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$146 total

Jul 5 - Jul 6

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.

Hyannis Plaza Hotel

662 Main Street Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$142 total

Jul 1 - Jul 2

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. There's a garden and multilingual staff can provide around-the-clock assistance.

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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

4.5/5(8 reviews)

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 $764. 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.