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Osterville Vacation Rentals

Our Favorite Vacation Rentals in Osterville

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Osterville Vacation Rentals with a Pool

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Osterville Vacation Rentals with Wi-Fi

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Osterville Pet-Friendly Vacation Rentals

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Osterville Travel Guide

Osterville is a wonderful place to visit for all traveler types. Osterville is situated in Massachusetts and is north of Martha's Vineyard. It's a great vacation getaway for family fun, a romantic break or a long weekend with friends. Osterville Massachusetts is famous for being a New England town at the western entrance to Cape Codand is sure to keep you entertained for days on end.

Things to Do in Osterville

From outdoors adventures to culture and history, there's an impressive range of things to do when visiting Osterville. First on your list should be the Osterville Historical Society, it's a must-see and great experience for first-time travelers here. The Wildlife refuge at Mass Audubon's Sampson's Island is also a wonderful activity. These are of course just some of the things to do while visiting Osterville. This charming city has many other activities to choose from its honestly just going to depend on what you're looking for. Another popular thing to do is is seeing Cape Cod by rail. The Cape Cod Central railroad takes riders past the sand dunes, cranberry bogs as well as other places only accessible by rail -- where adults and kids alike can make lasting memories!

Best Time to Visit Osterville

Plan a vacation to Osterville in the summer months -- when the weather is warm and conditions are ideal for exploring in nature.

Food in Osterville

The two best restaurants in Osterville are Chart Room, which is known for having some of the best seafood, and the equally delicious Dolphin restaurant.

Price and Availability in Osterville

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The most expensive month to stay in a vacation rental in Osterville is in April, while the cheapest month is in November. The most popular time to book a vacation rental in Osterville is in the high season in July. Osterville has its low season in November, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Osterville tends to be Monday, while the most expensive day tends to be Saturday. Vacation homes in Osterville tend to be busiest on Saturdays, while it tends to be much quieter on Mondays.

The Weather in Osterville

82º 41º
1.79
85º 48º
2.88
91º 50º
1.24
91º 53º
2.8
87º 47º
3.09
78º 30º
5.06
67º 15º
8.49
58º 16º
3.87
57º
3.79
56º
6.95
60º 18º
5.71
65º 24º
3.84
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Rainy days
This climate histogram shows you the weather patterns in Osterville. The warmest months in Osterville are June and May, when temperatures reach 91 ˚F. The coolest month is January, when temperatures drop to 1 ˚F. The wettest month in Osterville is November with 8.49 inches of rain, while the driest month is July with 1.24 inches of rain.

What Expert Travelers Think

Vacation Rentals in Osterville

Choose the perfect vacation rental for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Homeaway and others. AllTheRooms has 194 rentals, hotels and other great places to stay during your time in Osterville, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. For those traveling on a budget, the most economical place to stay in Osterville is available at $65 per night. On average, an accommodation in Osterville will cost you $740 per night.

If you need an internet connection during your stay in Osterville, then you can choose from over 104 places to stay that have WiFi internet. We have 6 accommodations that come with breakfast included. Fitness addicts can get a workout in during their stay by choosing from 6 accommodations that have gyms. If you're planning on arriving in Osterville by car, be sure to choose from 102 accommodations that provide parking.

AllTheRooms has 22 pet-friendly places to stay in Osterville, so if you're traveling with your pet you won't have any problems.

We aggregate vacation rentals, hotels and other unique accommodation types from many providers in Osterville, including 61 places to stay from Airbnb, 26 accommodations from VRBO and 21 places to stay from Homeaway

102 of our rentals in Osterville have been rated by previous guests. They rated 56% as excellent or good. You can instantly book any of 39 places to stay right now.

Destinations near Osterville