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.
Chapter House
Save 100% on your flight
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Hyannis (HYA)
A bar/lounge and a terrace are featured at this inn, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
Inn on Main
Save 100% on your flight
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Hyannis (HYA)
This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A garden, a snack bar/deli, and a library are also on offer.
Anchor In Distinctive Waterfront Lodging
Save 100% on your flight
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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
Save 100% on your flight
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
Top Osterville hotels deals
Iris Hotel Cape Cod
291 Jones Rd, Falmouth, MA
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $251 total per night
$251 total
Jul 20 - Jul 21
Total includes 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
Cape Sands Inn
149 Main St - RT 28, West Yarmouth, MA
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $147 total per night
$147 total
Jul 20 - Jul 21
Total includes 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
Bayside Resort Hotel
225 Route 28, West Yarmouth, MA
Free Cancellation
Reserve now, pay when you stay
$231 nightly
The price is $264 total per night
$264 total
Jul 20 - Jul 21
Total includes 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
Margaritaville Resort Cape Cod
1225 Iyannough Rd, Hyannis, MA
Free Cancellation
Reserve now, pay when you stay
$355 nightly
The price is $406 total per night
$406 total
Aug 18 - Aug 19
Total includes 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
Hyannis Harbor Hotel
213 Ocean St, Hyannis, MA
Free Cancellation
Reserve now, pay when you stay
$311 nightly
The price is $356 total per night
$356 total
Jul 30 - Jul 31
Total includes 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. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.
Pool
Free WiFi
Vineyard Harbor Motel - Private Beach
60 Beach Road, Vineyard Haven, MA
$299 nightly
The price is $334 total per night
$334 total
Jul 31 - Aug 1
Total includes taxes and fees
This motel features a terrace, barbecue grills, and free self parking. A picnic area and luggage storage are also provided.
On private beach
Parking included
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?
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.
Public Beach
Why not spend a lazy afternoon at Public Beach during your trip to Osterville?
Frequently asked questions
