Deals on vacations and trips to Osterville

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Osterville flight + hotel vacation packages

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

Courtyard Resort

2 out of 5
Price was $363, price is now $310 per person
$310
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Hyannis (HYA)
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Free self parking and a computer station are also offered on site.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $468, price is now $362 per person
$362
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Hyannis (HYA)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a snack bar/deli are also on offer.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $829, price is now $661 per person
$661
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Hyannis (HYA)
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.
Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

2.5 out of 5
Price was $396, price is now $331 per person
$331
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Hyannis (HYA)
This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG

3 out of 5
Price was $454, price is now $386 per person
$386
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Hyannis (HYA)
This hotel features an outdoor pool, an indoor pool, and a restaurant. Enjoy the gym and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Top Osterville hotels deals

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
$101 nightly
The price is $116 total per night
$116 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a 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
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
$198 nightly
The price is $226 total per night
$226 total
Dec 14 - Dec 15
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
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $79 total per night
$79 total
Dec 14 - Dec 15
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
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $133 total per night
$133 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $125 total per night
$125 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Parking included
Red Jacket Beach Resort

Red Jacket Beach Resort

3.5 out of 5
1 South Shore Drive South Yarmouth MA
Get rates
A private beach, 2 restaurants, and an indoor pool are all featured at this traditional hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Bring the family and enjoy the children's club, children's pool, and kid-friendly dining.
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

Dowses Beach

Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville?

Dowses Beach

Stand Up & Paddle Cape Cod

Take the family on an outing to Stand Up & Paddle Cape Cod during your trip to Osterville. Attend a sporting event or simply enjoy the seafood restaurants while you're in the area.

Stand Up & Paddle Cape Cod

Public Beach

Why not spend a lazy afternoon at Public Beach during your trip to Osterville?

Public Beach

Frequently asked questions

How much are vacation packages to Osterville?
Starting at just $310, flight and hotel packages are a fabulous way to stretch your vacation budget even further. Watch out Osterville — here you come!
Where can I get the best vacation package deals for Osterville?
Travelocity is the place to go to score an awesome Osterville package deal. Select from 400 partner airlines and 1,000,000 properties around the world and put together a travel itinerary that fits your style. With so many options at hand, you have inspiration galore for your next big adventure.
Why should I book my Osterville vacation package with Travelocity?
Whether you're planning a weeks-long vacation or a last-minute weekend trip, we have plenty of amazing destinations to choose from at an affordable rate. In addition, we offer round-the-clock support, superb service and a Price Match Guarantee. Save yourself money and time and lock in your dream vacation today.
Can I save on my Osterville car rental if I bundle it with my hotel or flight?
Combining your flight, car and hotel into an Osterville vacation package is a great way to score the best deal. Plus, having your own car rental gives you total freedom to find your way to all those landmarks you can't wait to see. Located 60 mi from Osterville, Fenway Park is one place that should be on your itinerary. Put together a driving playlist and make a day trip of it.
Which airport is best for Osterville?
Logan Intl. Airport (BOS) is one of the busiest airports in Osterville. It's situated 60 mi northwest of the bustling downtown area. Other options available to you are T.F. Green Airport (PVD) (55 mi away from central Osterville) and Martha's Vineyard Airport (MVY) (20 mi away from central Osterville).
What is there to do in Osterville?
Dowses Beach is one of the superb sights that make Osterville such a great place to visit. But allow some extra time to discover its lesser-known attractions too. This is often where the best vacation memories are created.
Where should I stay when visiting Osterville?
Many travelers choose to check in to the Charming 3-bedroom house in Osterville. It's an excellent base for your Osterville getaway.

Photos of local treasures

Browse Osterville vacation photos for more inspiration

Osterville featuring a bay or harbor and a coastal town
Osterville featuring signage
Osterville featuring signage
Osterville featuring a bay or harbor
Osterville showing signage