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.
Inn on Main

Inn on Main

3.5 out of 5
Price was $1,069, price is now $929 per person
$929
per person
Dec 6 - Dec 10
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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 garden, a snack bar/deli, and a library are also on offer.
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
Price was $1,914, price is now $1,624 per person
$1,624
per person
Nov 1 - Nov 8
just found
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
An outdoor pool is featured at this hotel, along with free self parking. There's a garden and multilingual staff can provide around-the-clock assistance.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $1,851, price is now $1,620 per person
$1,620
per person
Nov 1 - Nov 8
just found
Roundtrip non-stop flight included
Dallas (DFW) 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. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.
Courtyard Resort

Courtyard Resort

2 out of 5
Price was $1,464, price is now $1,329 per person
$1,329
per person
Nov 1 - Nov 8
just found
Roundtrip non-stop flight included
Dallas (DFW) 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, a garden, and a picnic area are also offered.
Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG

3 out of 5
Price was $1,546, price is now $1,452 per person
$1,452
per person
Nov 1 - Nov 8
just found
Roundtrip non-stop flight included
Dallas (DFW) 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

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
$199 nightly
The price is $228 total per night
$228 total
Oct 4 - Oct 5
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. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.
Pool
Hot Tub
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
$231 nightly
The price is $264 total per night
$264 total
Oct 12 - Oct 13
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
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
$133 nightly
The price is $152 total per night
$152 total
Oct 12 - Oct 13
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
Pet friendly
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $192 total per night
$192 total
Oct 12 - Oct 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
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

4 out of 5
135 Route 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $156 total per night
$156 total
Oct 13 - Oct 14
Total with taxes and fees
The hotel's indoor pool, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. A coffee shop, a garden, and a picnic area are also on offer.
Pool
Parking included
Lighthouse Inn

Lighthouse Inn

3 out of 5
1 Lighthouse Inn Rd West Dennis MA
$149 nightly
The price is $171 total per night
$171 total
Sep 27 - Sep 28
Total with taxes and fees
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
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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?
See properties

Frequently asked questions

How much are vacation packages to Osterville?
Starting at just $929, 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.