Orleans Vacation Packages 2025/2026 from $399

Orleans flight + hotel vacation packages

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

SpringHill Suites by Marriott Boston/Andover

Save 100% on your flight

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a snack bar/deli, and a grocery/convenience store are also on offer.

Hyatt Regency Boston Harbor

East Boston

Save 100% on your flight

per person

Sep 5 - Sep 10

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate perks like free WiFi and a free airport shuttle. Valet parking, a 24-hour business center, and a terrace are also offered.

The Beverly

Save 100% on your flight

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Express check-out and a virtual front desk are also provided.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

per person

Sep 4 - Sep 7

found 6 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.

The Club at New Seabury

Save 100% on your flight

per person

Aug 25 - Aug 29

just found

Roundtrip non-stop flight included

Detroit (DTW) to Boston (BOS)

A golf course, 2 restaurants, and 15 outdoor tennis courts are all featured at this smoke-free condo resort. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas. Enjoy the gym and unwind at the bar/lounge and beach bar.

Top Orleans hotels deals

Rodeway Inn Orleans - Cape Cod

48 Cranberry Hwy, Orleans, MA

Free Cancellation

Reserve now, pay when you stay

Get rates

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Olde Tavern Motel And Inn

151 Cranberry Hwy, Orleans, MA

Get rates

This motel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic area are also on offer.

Skaket Beach Motel

203 Cranberry Hwy, Orleans, MA

Get rates

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a library are also on offer.

Pool

Breakfast included

Riviera Beach Resort

327 South Shore Drive, South Yarmouth, MA

Get rates

A private beach and an indoor pool are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities.

Cape Sands Inn

149 Main St - RT 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Don't see what you're looking for?

See all available properties in Orleans

View all properties

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.

Jonathan Young Windmill

Jonathan Young Windmill is just one of the places to see in Orleans, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches or seek out the hiking trails.

Rock Harbor Beach

Why not spend a lazy afternoon at Rock Harbor Beach during your trip to Orleans? Stroll along the area's beaches or simply enjoy its seafood restaurants.

Frequently asked questions

How much are vacation packages to Orleans?

With vacation packages available from just $399, 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.