South Dennis Vacations 2026 from CA $1,010

South Dennis flight + hotel packages

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

The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,010

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Boston (BOS)

Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.

Boston Harbor Hotel

North End

CA $1,285

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Boston (BOS)

Book a stay at this 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.

Meco Hotel - Hostel

West End

CA $1,151

per person

Jul 28 - Jul 31

found 19 hours ago

Roundtrip flight included

Halifax (YHZ) to Boston (BOS)

Stay at this hostel in Boston. Enjoy free WiFi, a snack bar/deli, and housekeeping. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.

Hotel Ivy Boston Common

Bay Village

CA $1,316

per person

Jun 30 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

Sea Crest Beach Resort

CA $1,915

per person

Jul 5 - Jul 11

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Boston (BOS)

Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Silver Beach and Cataumet Arts Center 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 $232

CA $345 total

May 20 - May 21

includes taxes & fees

Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions Main Street Hyannis 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 $232

CA $266 total

May 31 - Jun 1

includes taxes & fees

Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Main Street Hyannis 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 $176

CA $217 total

May 20 - May 21

includes taxes & fees

Book a stay at this 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 Main Street Hyannis are located nearby.

Hyannis Travel Inn

18 North St Hyannis MA

CA $138

CA $158 total

May 25 - May 26

includes taxes & fees

Stay at this hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Main Street Hyannis and Hyannis Harbor are located nearby.

Pool

Hot tub

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

Free cancellation

Reserve now, pay when you stay

CA $98

CA $113 total

May 20 - May 21

includes taxes & fees

Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.

Pool

Hot tub

Chatham Bars Inn

297 Shore Rd Chatham MA

CA $655

CA $749 total

May 20 - May 21

includes taxes & fees

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 Mayo House are located nearby.

On private beach

Pool

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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.