Osterville Vacation Rentals

Our Favorite Vacation Rentals in Osterville

  • Barnstable Village 4BR w/ Yard
     4br Home/Apartment
    RedAwning
    From
    $436
  • Newly Remodeled Home - 2 Miles To Craigville Beach Home
     Country House
    Booking.com
    From
    $325
  • Cape Cod Get Away- Centerville-
     Home/Apartment
    HolidayLettings
    From
    $377
  • Coastal/Beach Access Cottage in Centerville
     3br Home/Apartment
    RedAwning
    From
    $496
  • Cottage
     Country House
    Booking.com
    From
    $141
  • Cozy Cape Cod getaway w/ screened porch & firepit - two miles to the beach!
     3br Home/Apartment
    HolidayLettings
    From
    $362
  • Windmill Home Overlooking Marsh
     4br Home/Apartment
    RedAwning
    From
    $695
  • Walk to beaches & ferries - Snow's Creek Waterview
     Country House
    Booking.com
    From
    $484

Check prices for these upcoming dates

Osterville Vacation Rentals with Wi-Fi

  • Charming Cape Cod Home by the Beach
     3br Home/Apartment
    RedAwning
    From
    $612
  • Charming Ocean View Beach House
     4br Home/Apartment
    RedAwning
    From
    $786
  • New Seaside 3BR w/ Water Views & Deck
     3br Home/Apartment
    RedAwning
    From
    $973
  • Near Coast & Bay - 3BR w/ Fire Pit
     3br Home/Apartment
    RedAwning
    From
    $531

Osterville Pet-Friendly Vacation Rentals

  • Treetops - Large House and Private Haven in Centerville Near Craigville Beach
    Nice4br Home/Apartment
    HolidayLettings
    From
    $488
  • New Listing! “The Fitz Inn” Beach Retreat
     3br Home/Apartment
    RedAwning
    From
    $651
  • Incredible 4 Acre Estate Pool Home, Lighted Tennis Court, Numerous Amenities!
     6br Home/Apartment
    HolidayLettings
    From
    $1,638
  • #901: Experience a Cape vacation in a NEW home. Completely renovated in 2015.
     4br Home/Apartment
    HolidayLettings
    From
    $383

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

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.

The Weather in Osterville

Rainy days
87 º47
3
78 º30
5
67 º15
8
58 º16
4
57 º1
4
56 º9
7
60 º18
6
65 º24
4
82 º41
2
85 º48
3
91 º50
1
91 º53
3
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Osterville. The hottest month in Osterville is May, when temperatures peak at 91 ˚F. The coolest month is December, when temperatures drop to 1 ˚F. The wettest month in Osterville is February with 8.49 inches of rain, while the driest month is June with 1.24 inches of rain.

What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — 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
  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat

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