Osterville Vacation Rentals

Compare 1,526 available properties from 18 providers
Osterville
Anytime
2 guests
Save up to 44%

Best Vacation Home Deals in Osterville

-29%
e.g. 3/16 - 3/23
House ∙ 8 guests ∙ 4 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $722 $1,022
VRBO
View deal
-32%
e.g. 9/7 - 9/14
House ∙ 10 guests ∙ 4 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $852 $1,253
VRBO
View deal
-44%
e.g. 3/16 - 3/23
House ∙ 7 guests ∙ 3 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $196 $348
VRBO
4.9
View deal

Find a dreamlike accommodation from $45 per night by searching and comparing the 1,526 properties listed in Osterville. Each of the properties from our partner websites are directly compared by our algorithm to help you save up to 44%.

Recommended Vacation Rentals in Osterville

Find your perfect vacation rental in Osterville: from $46 per night

House ∙ 6 guests ∙ 3 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $282
VRBO
5.0
View deal
House ∙ 7 guests ∙ 3 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $196
VRBO
4.9
View deal
House ∙ 2 guests ∙ 1 bedroom
Osterville, Barnstable, Massachusetts, United States
from $283
Airbnb
4.5
View deal
Cabin ∙ 2 guests
Osterville, Barnstable, Massachusetts, United States
from $333
Airbnb
5.0
View deal
Cottage ∙ 3 guests ∙ 1 bedroom
Osterville, Barnstable, Massachusetts, United States
from $171
Airbnb
5.0
View deal
House ∙ 4 guests
Osterville, Barnstable, Massachusetts, United States
from $189
Airbnb
5.0
View deal
House ∙ 4 guests ∙ 2 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $186
Airbnb
4.5
View deal
Condo ∙ 5 guests ∙ 2 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $362
Airbnb
5.0
View deal
Cottage ∙ 5 guests ∙ 3 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $310
Airbnb
5.0
View deal
See all offers

Vacation Rentals With Fireplaces

Fireplace
House ∙ 3 guests ∙ 2 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $239
VRBO
5.0
View deal
Fireplace
House ∙ 10 guests ∙ 5 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $250
VRBO
4.4
View deal
Fireplace
House ∙ 10 guests ∙ 6 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $792
Airbnb
5.0
View deal
See all offers

Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 10 guests ∙ 3 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $421
VRBO
5.0
View deal
Fishing
House ∙ 10 guests ∙ 4 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $888
VRBO
5.0
View deal
Fishing
House ∙ 8 guests ∙ 4 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $743
VRBO
5.0
View deal
See all offers

Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 20 guests ∙ 11 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $2,415
VRBO
5.0
View deal
Pet-friendly
House ∙ 4 guests ∙ 1 bedroom
Osterville, Barnstable, Massachusetts, United States
from $235
Airbnb
5.0
View deal
Pet-friendly
House ∙ 9 guests ∙ 4 bedrooms
Osterville, Barnstable, Massachusetts, United States
from $863
Airbnb
5.0
View deal
See all offers

Popular Rental Amenities in Osterville

  • Kitchen (196)
  • TV (194)
  • Internet (189)
  • AC (149)
  • Grill (145)
  • Microwave (142)
  • Washer (140)
  • Dishwasher (138)
  • Parking (125)
  • No smoking (123)
  • Fireplace (105)
  • No pets (90)
Our search page's filters will help you find the ideal vacation rental in Osterville. HomeToGo's data reveals that "TVs" and "internet" prove to be the most frequently provided features in Osterville. You could even look for rentals if you want a rental with a jacuzzi (30 rentals include "Jacuzzis" in Osterville) or if you want to sweat it out in a sauna (8 rentals in Osterville include "saunas").

The Weather in Osterville

39°
25°
39°
25°
45°
30°
55°
39°
66°
50°
73°
57°
81°
66°
79°
64°
73°
57°
63°
48°
52°
37°
46°
32°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. During July, maximum temperatures go up to more than 80° Conversely, January is the coolest month in Osterville, with temperatures going under 24° The rainiest month is February while the driest month is August.

Accommodations in Osterville

In Osterville, house rentals are the most common property type. Interestingly, the average rental fee for this specific accommodation type is $873 a night, with an average size of 2,820 ft². Furthermore, these properties are perfect for 9 it represents the average number of people house rentals can host in Osterville. If you are searching for another type of accommodation, you can find many other offers, such as private rooms, which are the other very typical type of property in Osterville. Our data shows that the average price of private rooms is $138 per night for an area of 1,080 ft².

Appreciate Cape Cod with Osterville vacation homes

Your comfortable vacation rental in Osterville, Massachusetts locates you in a charming seaside resort that blends small town affability with the sublime scenery of Cape Cod. The beach is never far away in this picturesque village, which is amply served with exciting seasonal events, especially for its size.

Show all 1,526 properties
Food & Drinks

Seaside suppers on Cape Cod

In the summer, the farmers' market at Osterville groans heavily with the weight of juicy and delicious produce, grown locally. Come and check out the stalls, which are also packed with homemade cakes, cookies, and other goodies.

The coastal location of Osterville guarantees fresh fish in the restaurants that line the marina too.

Family Activities

Water sports and seasonal festivals

Your whole family will adore sailing in Nantucket Sound, and will love the bike excursions along the coastal pathways.

Boating fans will be enamored of the marina's range of vessels, which you can easily charter and explore the area by sea. Don't miss the seasonal Village Days, which entail floats, food, and live music.

We compare more than 600 providers, including:

Booking.com Vacation Rentals in Osterville VRBO Vacation Rentals in Osterville HomeAway Vacation Rentals in Osterville Airbnb Vacation Rentals in Osterville TripAdvisor Vacation Rentals in Osterville VacationRentals.com Vacation Rentals in Osterville HouseTrip Vacation Rentals in Osterville FlipKey Vacation Rentals in Osterville 9flats.com Vacation Rentals in Osterville VaycayHero Vacation Rentals in Osterville PerfectPlaces.com Vacation Rentals in Osterville Homestay.com Vacation Rentals in Osterville Only-apartments Vacation Rentals in Osterville Interhome Vacation Rentals in Osterville Bedycasa Vacation Rentals in Osterville Novasol Vacation Rentals in Osterville HomeEscape Vacation Rentals in Osterville

Vacation Destinations Near Osterville