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.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $1,166, price is now $1,067 per person
$1,067
per person
Dec 3 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Hyannis (HYA)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
Price was $1,402, price is now $1,299 per person
$1,299
per person
Dec 4 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Hyannis (HYA)
A private beach, 6 restaurants, and 4 outdoor tennis courts are all featured at this luxury resort. Enjoy a day at the beach kayaking, or relax with beach umbrellas. There's fun for all ages with a children's club and a playground, and babysitting is an added bonus.
Inn on Main

Inn on Main

3.5 out of 5
Price was $1,317, price is now $1,239 per person
$1,239
per person
Dec 4 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Hyannis (HYA)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free cooked-to-order breakfast each morning. A snack bar/deli and a library are also provided.
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $1,327, price is now $1,267 per person
$1,267
per person
Dec 3 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Hyannis (HYA)
This resort's 3 outdoor tennis courts and seasonal outdoor pool are among the featured amenities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle. A garden, a picnic area, and laundry facilities are also on offer.
The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Price was $1,529, price is now $1,466 per person
$1,466
per person
Dec 3 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Hyannis (HYA)
This bed & breakfast features a terrace, barbecue grills, and free self parking. Enjoy the free local cuisine breakfast each morning. A garden and a picnic area are also provided.

Top Osterville hotels deals

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $193 total per night
$193 total
Nov 16 - Nov 17
Total with taxes and fees
A private beach, 2 restaurants, and an indoor pool are all 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 pool and an arcade/game room, and families will appreciate the picnic area.
On private beach
Pool
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $168 total per night
$168 total
Nov 30 - Dec 1
Total with taxes and fees
A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. A garden is provided and the front desk is staffed around-the-clock.
Pool
Free WiFi
Lighthouse Inn

Lighthouse Inn

3 out of 5
1 Lighthouse Inn Rd West Dennis MA
Get rates
A private beach and an outdoor tennis court are featured at this smoke-free hotel. Spend a day at the beach windsurfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with mini golf and a playground, and families will appreciate the onsite laundry facilities.
On private beach
Pool
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St Hyannis MA
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $113 total per night
$113 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and express check-out are also on offer.
Pool
Hot Tub
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

2.5 out of 5
1470 Iyannough Road Hyannis MA
Free Cancellation
$98 nightly
The price is $112 total per night
$112 total
Nov 30 - Dec 1
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 sauna and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
216 Main St West Yarmouth MA
Get rates
This hotel features an indoor pool and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A garden, a picnic area, and barbecue grills 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.

Stay near popular Osterville attractions

A wooden pier with a sunset view over the water.

Dowses Beach

10.0/10 (1 review)
Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville?
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Frequently asked questions

How much are vacation packages to Osterville?
Starting at just $1,067, 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

A house by a lake with boats.
Storefronts with signs for Coastal Style, Sara Campbell, and Oyster Island Emporium.
Storefronts including The Artistic Framers, Designers Walk, and Wax By Beauty.
A boat docked near a forested shoreline with other boats in the background.
A sign advertising Osterville as Cape Cod's lifestyle destination, available on Wednesdays on Wianno from July to August.