Osterville Vacation Rentals

Our Favorite Vacation Rentals in Osterville

  • Newly Remodeled Home - 2 Miles To Craigville Beach Home
     Country House
    Booking.com
    From
    $196
  • Cape Cod Get Away- Centerville-
     Home/Apartment
    HolidayLettings
    From
    $377
  • Hyannis Hideaway
     Country House
    Booking.com
    From
    $103
  • Contemporary Home < 3 Miles To Downtown & Beaches
     3br Home/Apartment
    HolidayLettings
    From
    $493
  • 181 Chase St Home
     Country House
    Booking.com
    From
    $209
  • Sunset Charter on Private Trawler Yacht 42'-
     2br Boat
    HolidayLettings
    From
    $885
  • Haven at Halfway Pond
     Country House
    Booking.com
    From
    $207
  • New Luxury Villa (B) Steps Away from the Beach
    Excellent5br Country House
    Flipkey
    From
    $708

Check prices for these upcoming dates

Osterville Vacation Rentals with a Pool

  • Cape Cod Cabana Getaway with Pool
    ExcellentHome/Apartment
    Airbnb
    From
    $234
  • Private home/cottage with pool. 2 miles to beach.
    ExcellentHome/Apartment
    Airbnb
    From
    $381
  • Magical home built around Windmill with ocean view
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,017

Osterville Vacation Rentals with Wi-Fi

  • Your dog will love it here and so will you!
    ExcellentHome/Apartment
    Airbnb
    From
    $107
  • Barnstable Village - Walk to Beach
    Excellent3br Home/Apartment
    Airbnb
    From
    $367
  • Peaceful apartment, near harbor!
    Excellent2br Home/Apartment
    Airbnb
    From
    $119
  • Cape Cod Seacoast Village Post & Beam
    Excellent3br Home/Apartment
    Airbnb
    From
    $297

Osterville Pet-Friendly Vacation Rentals

  • Treetops - Large House and Private Haven in Centerville Near Craigville Beach
    Nice4br Home/Apartment
    HolidayLettings
    From
    $488
  • Spacious Lake Front House w Stunning Scenary
     6br Home/Apartment
    HolidayLettings
    From
    $983
  • Sunny studio Cotuit, CapeCod, 2mi to the beach,sleeps 4, w /private entrance
     -1br Studio
    HolidayLettings
    From
    $238
  • Cozy Cape Cod getaway w/ screened porch & firepit - two miles to the beach!
     3br Home/Apartment
    HolidayLettings
    From
    $274

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
67° 15°
8
58° 16°
4
57°
4
56°
7
60° 18°
6
65° 24°
4
82° 41°
2
85° 48°
3
91° 50°
1
91° 53°
3
87° 47°
3
78° 30°
5
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — 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
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae

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