Book Exclusive South Dennis Vacation Packages

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South Dennis flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Price was CA $1,036, price is now CA $787 per person
CA $787
per person
May 1 - May 4
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,834, price is now CA $1,606 per person
CA $1,606
per person
May 1 - May 4
found 1 hour ago
Roundtrip flight included
Montreal (YUL) 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 Boston Common are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,818, price is now CA $1,225 per person
CA $1,225
per person
May 1 - May 4
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $2,193, price is now CA $1,583 per person
CA $1,583
per person
Mar 14 - Mar 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,078, price is now CA $819 per person
CA $819
per person
May 1 - May 4
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.

Top South Dennis hotels deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $320 total
Feb 10 - Feb 11
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 Cape Codder Water Park and Hyannis Golf Course are located nearby.
Pool
Hot tub
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $498 per night
CA $498
CA $570 total
Feb 11 - Feb 12
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 Chatham Fish Pier are located nearby.
On private beach
Pool
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mayo House and Chatham Windmill are located nearby.
Pool
Breakfast included
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street Brewster MA
The price is CA $218 per night
CA $218
CA $327 total
Feb 12 - Feb 13
includes taxes & fees
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Ocean Edge Golf Club and Linnell Landing Beach are located nearby.
On private beach
Pool
The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort

2.5 out of 5
41 Chase Ave Dennis Port MA
Get rates
Book a stay at this beach hotel in Dennis Port. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Sea Street Beach and Cape Cod Theatre Company – Home of the Harwich Jr. Theatre are located nearby.
On private beach
Pool
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

2.5 out of 5
867 Iyannough Road Hyannis MA
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
CA $193 total
Feb 15 - Feb 16
includes taxes & fees
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 John F. Kennedy Hyannis Museum are located nearby.
Pool
Breakfast included
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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.

Cape Cod Rail Trail

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 $787. 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.

Photos of local treasures

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South Dennis
South Dennis
South Dennis
Cold Storage Beach Dunes in Winter.
Cape cod