Orleans Vacation Packages 2026 from $592

Orleans flight + hotel vacation packages

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

The Cove at Yarmouth by Westgate Resorts

Save 100% on your flight

$592

per person

May 29 - Jun 3

found 12 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,436

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

The Revolution Hotel

South End

Save 100% on your flight

$1,178

per person

May 8 - May 15

found 19 hours ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Luxury 2BR near Cambridge

Prospect Hill

Save 100% on your flight

$1,725

per person

Jun 11 - Jun 15

just found

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

This apartment features a virtual front desk.

Thomas Sea Suites

Plymouth Downtown Waterfront District

Save 100% on your flight

$1,085

per person

May 29 - Jun 3

found 12 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. A rooftop terrace and a virtual front desk are also provided.

Top Orleans hotels deals

Private beach access Wrap around porch!

Orleans MA

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Pet friendly

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

$208 nightly

$238 total

Mar 22 - Mar 23

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. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Pool

Hot Tub

Aiden by Best Western Cape Cod - West Yarmouth

476 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$111 total

Mar 29 - Mar 30

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the 24-hour gym and perks like free self parking.

Pool

Breakfast included

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$141 total

Apr 12 - Apr 13

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

Chatham Bars Inn

297 Shore Rd Chatham MA

$368 nightly

$421 total

Mar 25 - Mar 26

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

Chatham Wayside Inn

512 Main St Chatham MA

Free Cancellation

Reserve now, pay when you stay

$157 nightly

$180 total

Mar 22 - Mar 23

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

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

Skaket Beach

4.5/5(18 reviews)

Warm, clear waters make this beach destination ideal for casual swimming, watersports or a restorative rest on the white sandy shore.

An evening at the Cape is just what the weather gods recommend. Come summer and most Bostonians don't lose a single opportunity to hit the coastline. These miles of pristine beaches make 100 days of summer absolutely worthwhile. Most people have a few cape stories, and so do we. Hoping to share them with you all over this summer.

#CapeCod #VisitMA

Rock Harbor Beach

Why not spend a lazy afternoon at Rock Harbor Beach during your trip to Orleans?

stony rock pier, ocean boardwalk, off-centered

Stony Island

Commune with nature and explore the great outdoors at Stony Island during your travels in Eastham. Amble around the area's beautiful beaches or seek out the biking trails.

Frequently asked questions

How much are vacation packages to Orleans?

With vacation packages available from just $592, it's not necessary to blow out the credit card for your trip to Orleans. Travelocity can help. Bundle your flights, hotels and experiences into a package and walk away with exciting discounts. The more you book, the greater the savings.

How long should my Orleans vacation be?

Many travelers pack their suitcase and explore the sights of Orleans for an average of 2 nights. That gives you a rough guide, but don't be limited by it. Whether you just stay a few nights to see the famous attractions or stick around to uncover off-the-beaten-path gems, an epic adventure awaits.

Where can I get the best vacation package deals for Orleans?

For the perfect package deal to Orleans, no one compares to Travelocity. Choose from 400 partner airlines and 1,000,000 worldwide properties to create your ultimate adventure — it couldn't be easier than that.

Why should I book my Orleans vacation bundle with Travelocity?

Because life is an amazing journey, and we've got everything you could hope for to help you on the way. With our exceptional service and Price Match Guarantee, you can organize your trip with confidence. And you can rest easy on the road knowing we've got you covered with our round-the-clock support.

Can I save on my Orleans car rental if I bundle it with a hotel or flight?

Bundling your hotel, car and flight into an Orleans vacation package is a surefire way to score an amazing deal. Plus, having your own rental car gives you total freedom to make your way to all those amazing sights you're itching to check out. Sitting 70 mi away from Orleans, Fenway Park is one place that should be on your must-do list. Top up the tank and make a day trip of it.

Which airport is best for Orleans?

Martha's Vineyard Airport (MVY), located around 40 mi southwest of downtown Orleans, is probably where you'll step off the plane. Your other options are Nantucket Memorial Airport (ACK) (35 mi away from central Orleans) and Provincetown Municipal Airport (PVC) (25 mi away from central Orleans).

What is there to do in Orleans?

Orleans is teeming with places to discover, including Rock Harbor Beach and Orleans Bowling Center. These well-known attractions are at the top of most visitors' travel schedules.

Where should I stay when visiting Orleans?

Many people stay at the Olde Tavern Motel And Inn. It's a terrific base for your Orleans vacation.