South Dennis Vacation Packages 2026 from $476

South Dennis flight + hotel vacation packages

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

The Colonnade Hotel Back Bay

Back Bay

Save 100% on your flight

$476

per person

Feb 14 - Feb 17

found 24 hours ago

Roundtrip flight included

Philadelphia (PHL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, 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.

The McKernan Inn

$562

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip non-stop flight included

New Orleans (MSY) to Boston (BOS)

This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.

The Dagny Boston

Downtown Boston

$728

per person

Mar 16 - Mar 19

just found

Roundtrip non-stop flight included

New Orleans (MSY) 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-out, and valet parking. A coffee shop, a library, and a computer station are also on offer.

Hotel Commonwealth

Fenway–Kenmore

$644

per person

Mar 16 - Mar 19

just found

Roundtrip non-stop flight included

New Orleans (MSY) to Boston (BOS)

This smoke-free hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the laundry service, conference space, and valet parking. A lobby fireplace, luggage storage, and concierge services are also on offer.

Omni Parker House

Downtown Boston

$700

per person

Mar 16 - Mar 19

just found

Roundtrip non-stop flight included

New Orleans (MSY) to Boston (BOS)

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

Top South Dennis hotels deals

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$126 total

Jan 1 - Jan 2, 2026

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

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$221 total

Dec 24 - Dec 25

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

Dec 24 - Dec 25

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

Chatham Bars Inn

297 Shore Rd Chatham MA

$304 nightly

$348 total

Dec 24 - Dec 25

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

Red Jacket Beach Resort

1 South Shore Drive South Yarmouth MA

Get rates

A private beach, 2 restaurants, and an indoor pool are all featured at this traditional hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Bring the family and enjoy the children's club, children's pool, and kid-friendly dining.

On private beach

Pool

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$114 total

Jan 6 - Jan 7, 2026

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

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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 $476. 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.