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Osterville Vacation Rentals

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Our Favorite Vacation Rentals in Osterville

  • Barnstable Village 4BR w/ Yard
     4br Home/Apartment
    RedAwning
    From
    $376
  • West Bayview
     Country House
    Booking.com
    From
    $139
  • Lovely tidal marsh views with short walk to beach
     4br Home/Apartment
    HolidayLettings
    From
    $524
  • Newly Remodeled Home - 2 Miles to Craigville Beach
     4br Home/Apartment
    RedAwning
    From
    $646
  • Meet Me at the Cape
     Country House
    Booking.com
    From
    $112
  • Cape Cod Get Away- Centerville-
     Home/Apartment
    HolidayLettings
    From
    $377
  • Coastal/Beach Access Cottage in Centerville
     3br Home/Apartment
    RedAwning
    From
    $495
  • 3 Bed 1 Bath Vacation home in West Yarmouth
     Country House
    Booking.com
    From
    $136
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Osterville Vacation Rentals with a Pool

  • Cape Cod Cabana Getaway with Pool
    ExcellentHome/Apartment
    Airbnb
    From
    $234
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Osterville Vacation Rentals with Wi-Fi

  • Charming Cape Cod Home by the Beach
     3br Home/Apartment
    RedAwning
    From
    $616
  • New Seaside 3BR w/ Water Views & Deck
     3br Home/Apartment
    RedAwning
    From
    $1,304
  • New Listing! “The Fitz Inn” Beach Retreat
     3br Home/Apartment
    RedAwning
    From
    $655
  • New Listing! Seabreeze Village Retreat Near Beach
     3br Home/Apartment
    RedAwning
    From
    $716
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Osterville Pet-Friendly Vacation Rentals

  • Keyes Beach Retreat
    Excellent4br Country House
    Flipkey
    From
    $608
  • Treetops - Large House and Private Haven in Centerville Near Craigville Beach
    Nice4br Home/Apartment
    HolidayLettings
    From
    $488
  • Cape Cod Cottage
     2br Home/Apartment
    HolidayLettings
    From
    $252
  • #901: Experience a Cape vacation in a NEW home. Completely renovated in 2015.
     4br Home/Apartment
    HolidayLettings
    From
    $484
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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.

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Price and Availability in Osterville

Most expensive
Most availability
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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 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.
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The Weather in Osterville

Rainy days
62° 10°
3
59° 9°
4
68° 21°
5
76° 35°
4
84° 47°
6
94° 56°
4
86° 49°
2
81° 42°
4
80° 34°
7
68° 19°
4
58° 15°
8
61° 5°
5
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Osterville. The warmest months in Osterville are June and May, when temperatures reach 94 ˚F. The coolest month is December, when temperatures drop to 5 ˚F. The wettest month in Osterville is January with 8.33 inches of rain, while the driest month is May with 2.11 inches of rain.

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What Expert Travelers Think

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
    Visit Coco Travels

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
    LTL Mandarin School

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
    Visit Amanda Alston

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