South Dennis Vacation Packages 2026 from $507

South Dennis flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

$507

per person

Jan 19 - Jan 24

found 4 hours ago

Roundtrip flight included

Houston (HOU) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Harbor Hotel Provincetown

$10,711

per person

Jan 22 - Jan 25

found 17 hours ago

Roundtrip flight included

Los Angeles (LAX) to Provincetown (PVC)

This hotel features a bar/lounge, a poolside bar, and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and a picnic area are also on offer.

Boston Harbor Hotel

North End

$1,101

per person

Jan 11 - Jan 14

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

Four Seasons Hotel Boston

Bay Village

$1,372

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Houston (HOU) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

The Langham, Boston

Downtown Boston

$974

per person

Jan 11 - Jan 14

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

Top South Dennis hotels deals

Cape Cod's "Beach Rose"

Dennis MA

Get rates

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Chatham Bars Inn

297 Shore Rd Chatham MA

$353 nightly

$404 total

Nov 11 - Nov 12

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

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$145 total

Nov 15 - Nov 16

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 free continental breakfast each morning.

Pool

Breakfast included

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$78 total

Nov 9 - Nov 10

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

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$137 total

Dec 1 - Dec 2

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

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$128 total

Nov 9 - Nov 10

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.

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.

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Frequently asked questions

How much are vacation packages to South Dennis?

You can land an amazing flight and hotel bundle for as low as $507. 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.