South Dennis Vacations 2025 from CA $1,010

South Dennis flight + hotel packages

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

Global Luxury Suites East Boston

East Boston

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 4-star family-friendly aparthotel in Boston. Enjoy free WiFi, free parking, and a fitness center. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Boston Harbor Hotel

North End

Save 100% on your flight

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Hyatt Place Boston/Medford

Save 100% on your flight

per person

May 21 - May 26

found 23 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Boston (BOS)

Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Encore Boston Harbor and Harvard Square are located nearby.

Encore Boston Harbor

Save 100% on your flight

per person

Apr. 21 - Apr. 25

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

The Westin Boston Seaport District

Seaport District

Save 100% on your flight

per person

Apr. 21 - Apr. 25

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Top South Dennis hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd, Hyannis, MA

Free cancellation

Reserve now, pay when you stay

CA $229

CA $311 total

includes taxes & fees

19 Mar - 20 Mar

Stay at this 4-star family-friendly resort in Hyannis. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the clean rooms in our reviews. Popular attractions Cape Codder Water Park and Hyannis Harbor are located nearby.

Pool

Hot tub

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road, Hyannis, MA

Free cancellation

Reserve now, pay when you stay

CA $147

CA $168 total

includes taxes & fees

23 Mar - 24 Mar

Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Cape Codder Water Park and Hyannis Harbor are located nearby.

Pool

Breakfast included

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

Free cancellation

Reserve now, pay when you stay

CA $135

CA $171 total

includes taxes & fees

12 Mar - 13 Mar

Stay at this 3-star beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.

Pool

Hot tub

Chatham Bars Inn

297 Shore Rd, Chatham, MA

CA $375

CA $451 total

includes taxes & fees

12 Mar - 13 Mar

Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Chatham Fish Pier are located nearby.

On private beach

Pool

Hampton Inn & Suites Cape Cod-West Yarmouth

99 Main Street, Route 28, West Yarmouth, MA

Free cancellation

Reserve now, pay when you stay

CA $134

CA $153 total

includes taxes & fees

23 Mar - 24 Mar

Book a stay at this family-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.

Pool

Hot tub

Comfort Inn Hyannis - Cape Cod

259 Main Street, Hyannis, MA

Free cancellation

Reserve now, pay when you stay

CA $137

CA $156 total

includes taxes & fees

19 Mar - 20 Mar

Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.

Pool

Hot tub

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See all available properties in South Dennis

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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

5/5(1 review)

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.

South Dennis Vacations

If you're taking a trip to South Dennis and you don't really know a lot about it, there's no need to worry — we'll give you the lowdown!

South Dennis is a neighborhood in Cape Cod. To get there, travel 5 miles (8 kilometers) to the southeast of the center of town.

Places to visit in South Dennis

In the mood to venture into the great outdoors? The wide expanse at Wilbur Park is a wonderful place to play some sports or simply stop and put your feet up. Need some more close by options? Throughout the ages, people have built sky-high structures for many reasons. Come and discover the story behind Scargo Tower — you won't have trouble spotting it! But there's more. Whether they're tucked away under ice-capped mountains or a much-needed oasis in the middle of a dry and hot landscape, there's something truly magical about lakes. Head out and discover how the view looks at Follins Pond.

Where do you fly into for South Dennis?

If you're vacationing in South Dennis, the closest major terminal is Barnstable Municipal Airport (HYA). It's roughly 8 miles (13 kilometers) to the southwest from the central area. Choose an in-flight film, get comfortable and you'll be there before you know it.

Frequently asked questions

How much are vacation packages to South Dennis?

You can land an amazing flight and hotel bundle for as low as CA $1,010. 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 105 kilometers from South Dennis.

Which airport is best for South Dennis?

Martha’s Vineyard Airport (MVY), located around 56 kilometers southwest of downtown South Dennis, is most likely where you’ll touch down. Your other choices are Nantucket Memorial Airport (ACK) (48 kilometers away from central South Dennis) and Provincetown Municipal Airport (PVC) (40 kilometers 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.