South Dennis Vacation Packages 2026 from $1,192

South Dennis flight + hotel vacation packages

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

The Langham, Boston

Downtown Boston

Save 100% on your flight

$1,192

per person

Dec 2 - Dec 6

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Boston Harbor Hotel

North End

$1,298

per person

Nov 24 - Nov 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Luxury Apartments by Hyatus at Boston Everett

Save 100% on your flight

$11,192

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

This apartment features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.

The Monty Boston

Downtown Boston

Save 100% on your flight

$2,595

per person

Nov 21 - Nov 27

found 3 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

A rooftop terrace is featured at this aparthotel, along with free WiFi in public areas and a garden. Laundry facilities and a virtual front desk are also provided.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$1,286

per person

Nov 21 - Nov 27

found 3 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.

Top South Dennis hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$211 total

Oct 25 - Oct 26

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. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.

Pool

Hot Tub

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$148 total

Oct 27 - Oct 28

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

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA

$104 nightly

$119 total

Oct 4 - Oct 5

Total with taxes and fees

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.

On private beach

Pool

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA

Free Cancellation

$115 nightly

$132 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$156 total

Oct 13 - Oct 14

Total with taxes and fees

The hotel's indoor pool, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. A coffee shop, a garden, and a picnic area are also on offer.

Pool

Parking included

The Villages at Ocean Edge

One Villages Drive Brewster MA

$172 nightly

$197 total

Oct 19 - Oct 20

Total with taxes and fees

This smoke-free resort features a private beach, a golf course, and a full-service spa. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

On private beach

Pool

Don't see what you're looking for?

See all available properties in South Dennis

View all properties

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.

Stay near popular South Dennis attractions

Cape Cod Rail Trail

9.2/10 (10 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.

See properties

Frequently asked questions

How much are vacation packages to South Dennis?

You can land an amazing flight and hotel bundle for as low as $1,192. 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.