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Osterville Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Bed & Breakfast
Apartment
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

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Save up to 82%

Best Vacation Home Deals in Osterville

House Osterville
Apr 23 - Apr 30
-52%
$825
$400 per night
House ∙ 12 guests ∙ 6 bedrooms
Vacation Home in Marstons Mills with In-Ground Pool + Beautiful Views
5.0
"Excellent" (60 ratings)
Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Apr 23 - Apr 30
-32%
$529
$362 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Family Friendly Cottage in New Seabury with Yard & Grill + Beach Nearby
5.0
"Excellent" (30 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Apr 15 - Apr 22
-82%
$481
$89 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Mashpee Neck with Yard & Grill
4.8
"Excellent" (54 ratings)
Osterville, Barnstable, Massachusetts, United States
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Find a dreamlike accommodation from $118 per night by searching and comparing the 130 properties listed in Osterville. Each of the properties from our partner websites are directly compared by our algorithm to help you save up to 75%.

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Top-Rated Rentals and Accommodations in Osterville

Cottage Osterville
Feb 24 - Mar 2
$158 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Cottage in Centerville with Yard & Grill
4.9
"Excellent" (112 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Mar 23 - Mar 30
-45%
$257
$141 per night
House ∙ 7 guests ∙ 4 bedrooms
Wonderful House in Mashpee with Yard & Grill
4.8
"Excellent" (112 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Apr 18 - Apr 25
-22%
$226
$177 per night
House ∙ 2 guests ∙ 1 bedroom
Beautiful House in Centerville with Grill + Amazing Views
5.0
"Excellent" (34 ratings)
Osterville, Barnstable, Massachusetts, United States
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Recommended Vacation Rentals in Osterville

Find your perfect vacation rental in Osterville: from $118 per night

House Osterville
Oct 11 - Oct 18
$281 per night
House ∙ 10 guests ∙ 5 bedrooms
Lovely Vacation Home in Centerville with Grill & Yard
5.0
"Excellent" (55 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
May 16 - May 23
$855 per night
House ∙ 10 guests ∙ 5 bedrooms
Family Friendly Lovely House in Popponesset with Grill & Yard
5.0
"Excellent" (22 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 9 - Sep 16
$280 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Osterville with Grill & Yard
5.0
"Excellent" (23 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Oct 11 - Oct 18
$600 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Centerville with Grill & Yard
4.9
"Excellent" (35 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 23 - Sep 30
$213 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Centerville with 2-Car Garage
4.9
"Excellent" (23 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Nov 17 - Nov 24
-41%
$680
$400 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Centerville with Grill & Yard
5.0
"Excellent" (8 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Apr 23 - Apr 30
-55%
$1,000
$450 per night
House ∙ 6 guests ∙ 3 bedrooms
Pleasant House in New Seabury with Yard & Grill + Water Views
Osterville, Barnstable, Massachusetts, United States
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House Osterville
May 6 - May 13
-36%
$522
$332 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Mashpee Neck with Yard & Grill
4.9
"Excellent" (40 ratings)
Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Mar 22 - Mar 29
-53%
$258
$130 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Centerville with Grill & Yard
5.0
"Excellent" (52 ratings)
Osterville, Barnstable, Massachusetts, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Osterville

House Osterville
Oct 28 - Nov 4
-40%
$327
$195 per night
House ∙ 6 guests ∙ 2 bedrooms
Wonderful House in Hyannis with Grill & Yard
5.0
"Excellent" (58 ratings)
Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Oct 14 - Oct 21
-42%
$329
$191 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Centerville with Grill
4.5
"Outstanding" (28 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Nov 4 - Nov 11
-49%
$352
$181 per night
House ∙ 8 guests ∙ 3 bedrooms
House in West Hyannisport with Yard & Grill
5.0
"Excellent" (115 ratings)
Osterville, Barnstable, Massachusetts, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Osterville and book a vacation rental with air conditioning.

Cottage Air conditioning Osterville
Oct 7 - Oct 14
$158 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Cottage in Centerville with Yard & Grill
4.9
"Excellent" (112 ratings)
Osterville, Barnstable, Massachusetts, United States
Air conditioning
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House Air conditioning Osterville
Sep 9 - Sep 16
$280 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Osterville with Grill & Yard
5.0
"Excellent" (23 ratings)
Osterville, Barnstable, Massachusetts, United States
Air conditioning
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House Air conditioning Osterville
Nov 22 - Nov 29
-41%
$680
$400 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Centerville with Grill & Yard
5.0
"Excellent" (8 ratings)
Osterville, Barnstable, Massachusetts, United States
Air conditioning
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Vacation homes and rentals with a yard

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Osterville with private yards.

House Yard Osterville
Oct 28 - Nov 4
-40%
$325
$195 per night
House ∙ 6 guests ∙ 2 bedrooms
Wonderful House in Hyannis with Grill & Yard
5.0
"Excellent" (58 ratings)
Osterville, Barnstable, Massachusetts, United States
Yard
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Cottage Yard Osterville
Apr 23 - Apr 30
-32%
$529
$362 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Family Friendly Cottage in New Seabury with Yard & Grill + Beach Nearby
5.0
"Excellent" (30 ratings)
Osterville, Barnstable, Massachusetts, United States
Yard
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House Yard Osterville
Oct 11 - Oct 18
-45%
$256
$140 per night
House ∙ 7 guests ∙ 4 bedrooms
Wonderful House in Mashpee with Yard & Grill
4.8
"Excellent" (112 ratings)
Osterville, Barnstable, Massachusetts, United States
Yard
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Osterville accommodation with high-speed internet.

House Internet Osterville
Dec 9 - Dec 16
-62%
$564
$214 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Osterville with Spacious Patio
5.0
"Excellent" (2 ratings)
Osterville, Barnstable, Massachusetts, United States
Internet
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House Internet Osterville
Apr 23 - Apr 30
-21%
$229
$182 per night
House ∙ 2 guests ∙ 1 bedroom
Beautiful House in Centerville with Grill + Amazing Views
5.0
"Excellent" (34 ratings)
Osterville, Barnstable, Massachusetts, United States
Internet
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House Internet Osterville
Apr 1 - Apr 8
-62%
$643
$247 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Osterville with Grill
5.0
"Excellent" (8 ratings)
Osterville, Barnstable, Massachusetts, United States
Internet
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Popular Rental Amenities in Osterville

  • Internet (714)
  • TV (704)
  • Kitchen (684)
  • Air conditioning (680)
  • No smoking (655)
  • Microwave (642)
  • Grill (615)
  • Washer (584)
  • Dishwasher (533)
  • No pets (464)
  • Yard (385)
  • Fireplace (355)

Our search page's filters will help you find the ideal vacation rental in Osterville. HomeToGo's data reveals that "Internet" and "TV" prove to be the most frequently provided features in Osterville. You could even look for rentals if you want to sweat it out in a sauna (3 rentals include "Detached" in Osterville) or if you want to sweat it out in a sauna (3 rentals in Osterville include "Sauna").

The Weather in Osterville

max.
Min.
39°
25°
16 days 16
max.
Min.
39°
25°
17 days 17
max.
Min.
45°
30°
15 days 15
max.
Min.
55°
39°
12 days 12
max.
Min.
66°
50°
14 days 14
max.
Min.
73°
57°
11 days 11
max.
Min.
81°
66°
10 days 10
max.
Min.
79°
64°
9 days 9
max.
Min.
73°
57°
10 days 10
max.
Min.
63°
48°
14 days 14
max.
Min.
52°
37°
12 days 12
max.
Min.
46°
32°
17 days 17
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 81° Conversely, January is the coolest month in Osterville, with temperatures going under 25° The rainiest month is February while the driest month is August.

7-Day Weather Forecast in Osterville

Tue, 21 Mar
48°
37°

0%

11 h

9 mi/h

Wed, 22 Mar
51°
41°

0%

4 h

6 mi/h

Thu, 23 Mar
48°
46°

15%

0 h

12 mi/h

Fri, 24 Mar
44°
41°

15%

0 h

5 mi/h

Sat, 25 Mar
44°
41°

15%

1 h

13 mi/h

Sun, 26 Mar
50°
44°

10%

6 h

18 mi/h

Mon, 27 Mar
51°
39°

0%

9 h

9 mi/h

Accommodations for your vacation in Osterville

In Osterville, house rental are the most common property type. Interestingly, the average rental fee for this specific accommodation type is $816 a night, with an average size of 204 m². Furthermore, these properties are perfect for 8 it represents the average number of people house rental can host in Osterville. If you are searching for another type of accommodation, you can find many other offers, such as cabin, which are the other very typical type of property in Osterville. Our data shows that the average price of cabin is $458 per night for an area of 79 m².
Where to find the best food in Osterville?

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.

What are the best activities for families in Osterville?

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.

Information about vacation rentals in Osterville

🏡 Vacation rentals 132 properties
💳 Possible discounts up to 61%
🌙 Nightly prices starting at $89
⭐ Popular amenities Internet, TV and Kitchen
🐾 Pet friendly accommodations 225 properties
🏊 Vacation rentals with pools 82 properties

Frequently Asked Questions

What is the nightly price for a vacation rental in Osterville?

The price of a night's stay in Osterville starts at $89. If you would like to stay in a house rental, the average price is $816 per night. A cabin Osterville will cost $458 per night on average.

How many vacation rentals are available to book in Osterville?

Currently there are 132 vacation rentals from 6 providers in Osterville.

What are the most popular amenities for vacation rentals in Osterville?

If you're looking to book a vacation rental in Osterville, others search for accommodation with Internet, TV and Kitchen.

How many vacation rentals with a pool are there in Osterville?

Choose from 82 vacation rentals available to book in Osterville.

Are dogs allowed in vacation homes in Osterville?

Yes, there are 225 vacation rentals in Osterville that allow dogs , with an average price of $799 per night.

What's the best month to travel to Osterville?

Osterville has its warmest time of year around July and August, with average prices of $89 per night.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Osterville TripAdvisor Vacation Rentals in Osterville Vrbo Vacation Rentals in Osterville VacationRentals.com Vacation Rentals in Osterville HouseTrip Vacation Rentals in Osterville FlipKey Vacation Rentals in Osterville Homestay.com Vacation Rentals in Osterville Only-apartments Vacation Rentals in Osterville Interhome Vacation Rentals in Osterville Novasol Vacation Rentals in Osterville HomeEscape Vacation Rentals in Osterville

Vacation Destinations Near Osterville

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