A house by a lake with boats.

Find 5 Star Hotels in Osterville, MA from $156

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Check availability on Osterville 5 Star Hotels

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Osterville 5-star hotels

A spacious living area with a dining table, sofas, and a view of the sea.
A resort with a swimming pool, outdoor seating, and a view of the lake.
A spacious living room with a fireplace, comfortable seating, and a staircase leading to another area.
A garden with hydrangea bushes, a white picket fence, and a brick pathway leading to a building with a porch.

1. Harbor View Hotel

Harbor View Hotel
Edgartown
United States
Eryn
$373 nightly
$416 total
Oct 19 - Oct 20
Total with taxes and fees
Harbor View Hotel
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Osterville.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA
$207 nightly
$237 total
Oct 12 - Oct 13
Total with taxes and fees
Margaritaville Resort Cape Cod
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA
$137 nightly
$156 total
Oct 13 - Oct 14
Total with taxes and fees
9.2/10 Wonderful! (340 reviews)
Uncommoner Hotel by Reverie Boutique Collection
Faraway Martha's Vineyard

Faraway Martha's Vineyard

23 Kelly Street Edgartown MA
$307 nightly
$343 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Faraway Martha's Vineyard
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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.

Learn more about Osterville

Elegant boutiques and seafood restaurants line Main Street in this charming Cape Cod village with New England coastal appeal. Spend sunny afternoons at Joshua's Pond or Dowses Beach, where calm waters welcome swimmers and kayakers.

See all hotels in Osterville
Storefronts with signs for Coastal Style, Sara Campbell, and Oyster Island Emporium.

Top Osterville Hotel Reviews

Find out more about Osterville

Why not request the best of accommodations during your excursion to Osterville? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Osterville so popular in the last year. There's no reason to delay a getaway to Osterville any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Osterville are the perfect places to relax in when you really need to escape. What are you waiting for?

Book the Best Osterville 5-Star Hotels

You'll have a fantastic time at one of these 5-star hotels. High-end restaurants, excellent customer care, and rejuvenating spa offerings are all on offer. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready to kick back and indulge. What creature comforts do you want in your lodging? A mud wrap treatment that will leave you feeling like a million bucks? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A deep-tissue massage to help your cares fall away?

Ready for experiences outside your hotel room? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Osterville are waiting for you to relax after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Your Getaway Starts Today

The results are in, and Osterville 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Decide on one of our Osterville 5-star hotels today and relax in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Osterville?
The amount you pay for a 5-star hotel in Osterville can vary according to when you prefer to travel and how long you plan to be away, among a number of factors. Take advantage of our price per night filter and other search tools to score the best deal on a high-end stay.
  • Search for the lowest price per night from $156
What makes a hotel 5 stars in Osterville?
From fine dining restaurants and 24-hour gyms to pools and dreamy bedding, the 5-star experience in Osterville is all about relaxation and luxury. But it calls for more than just top-notch perks to get a 5-star rating. Hotels must also offer superb guest-focused services like beauty treatments, on-site laundry and 24/7 room service.
Are there any 5-star all-inclusive resorts in Osterville?
Use our handy filters to find an upmarket getaway in Osterville where most of what you need is included. After your initial search, narrow down your results for accommodations that have a rating of 5 stars and are described as "All inclusive." The most important thing on the agenda at these stays? Pure relaxation and indulgence.

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