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Osterville Vacation Rentals

Find 729 available offers from 7 partners
Osterville
Anytime
Guests
Osterville
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Osterville

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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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Vacation Houses With Pools

Make a splash on your next vacation! Over 15% of in Osterville vacation rentals have a swimming pool.

House  Osterville
Jun 8 - Jun 15
-29%
$430
$303 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Sandwich with Grill, Pool & Yard

4.4
Very good (25 ratings)
Osterville, Barnstable, Massachusetts, United States
Pool
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House  Osterville
Oct 12 - Oct 19
-17%
$821
$682 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Mashpee Neck with Patio, Pool & Yard

4.8
Outstanding (17 ratings)
Osterville, Barnstable, Massachusetts, United States
Pool
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House  Osterville
Sep 14 - Sep 21
$786 per night
House ∙ 11 guests ∙ 5 bedrooms

House in Marstons Mills with Landscaped Pool

4.9
Outstanding (23 ratings)
Osterville, Barnstable, Massachusetts, United States
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Osterville!

House  Osterville
Jun 1 - Jun 8
-66%
$746
$250 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Sandwich with Grill, Pool & Patio

4.4
Very good (25 ratings)
Osterville, Barnstable, Massachusetts, United States
Pet-friendly
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House  Osterville
Aug 18 - Aug 25
$309 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Marstons Mills with Grill & Yard

4.7
Excellent (12 ratings)
Osterville, Barnstable, Massachusetts, United States
Pet-friendly
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Cottage  Osterville
Sep 7 - Sep 14
$260 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Rental Cottage in Centerville with Grill & Patio

4.6
Excellent (34 ratings)
Osterville, Barnstable, Massachusetts, United States
Pet-friendly
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Osterville with their own private patios and balconies.

House  Osterville
Jun 22 - Jun 29
$1,496 per night
House ∙ 24 guests ∙ 7 bedrooms

Beautiful House in Barnstable with Sauna, Patio & Yard

4.2
Very good (5 ratings)
Osterville, Barnstable, Massachusetts, United States
Free cancellation
Balcony
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House  Osterville
Sep 16 - Sep 23
$572 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Osterville with Grill, Yard & Patio

5.0
Outstanding (25 ratings)
Osterville, Barnstable, Massachusetts, United States
Balcony
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House  Osterville
Sep 16 - Sep 23
$560 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Centerville with Grill, Yard & Patio

4.8
Outstanding (10 ratings)
Osterville, Barnstable, Massachusetts, United States
Balcony
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Best Vacation Home Deals in Osterville

Save up to 44%

House Osterville
Sep 16 - Sep 23
-43%
$265
$150 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Centerville with Grill, Patio & Yard

4.2
Very good (5 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 16 - Sep 23
-36%
$733
$472 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in West Barnstable with Pool, Patio & Grill

4.4
Very good (6 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 16 - Sep 23
-44%
$1,061
$594 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Centerville with Grill, Jacuzzi & Pool

Osterville, Barnstable, Massachusetts, United States
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Find a dreamlike accommodation from $150 per night by searching and comparing the 729 properties listed in Osterville. Each of the properties from our partner websites are directly compared by our algorithm to help you save up to 61%.

Recommended Vacation Rentals in Osterville

Find your perfect vacation rental in Osterville: from $150 per night

House Osterville
Sep 16 - Sep 23
$271 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Centerville with Grill

Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 7 - Sep 14
-37%
$293
$186 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Centerville with Free Parking

4.9
Outstanding (51 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 16 - Sep 23
$423 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Centerville with Grill

Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 14 - Sep 21
$159 per night
House ∙ 7 guests ∙ 4 bedrooms

Wonderful House in Mashpee with Yard, Grill & Patio

4.8
Outstanding (112 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 16 - Sep 23
$810 per night
House ∙ 16 guests ∙ 6 bedrooms

Lovely House in Centerville with Yard, Pool & Patio + Panoramic Views

4.8
Outstanding (49 ratings)
Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Sep 16 - Sep 23
$312 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Beautiful Cottage in Marstons Mills with Yard, Patio & Grill

5.0
Outstanding (2 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
May 18 - May 25
$295 per night
House ∙ 6 guests ∙ 3 bedrooms

Quiet House in Cotuit with Grill, Patio & Yard

5.0
Outstanding (36 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 17 - Sep 24
$571 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in New Seabury with Grill

5.0
Outstanding (2 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Oct 12 - Oct 19
-65%
$471
$167 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Cotuit with Patio, Grill & Yard + Sweeping Views

4.9
Outstanding (39 ratings)
Osterville, Barnstable, Massachusetts, United States
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Budget-friendly Vacation Rentals in Osterville

Find Fantastic yet Inexpensive Offers

Cottage Osterville
Aug 24 - Aug 31
$279 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Great Cottage in Centerville with Yard, Patio & Grill + Water View

4.6
Excellent (18 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 16 - Sep 23
$543 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Centerville with Ample Parking

4.5
Excellent (16 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Aug 24 - Aug 31
$349 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Centerville with Free Parking

4.9
Outstanding (51 ratings)
Osterville, Barnstable, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Osterville

Book Vacation Rental Offers with the Highest User Rating

House Osterville
Sep 16 - Sep 23
$1,080 per night
House ∙ 20 guests ∙ 7 bedrooms

House in Centerville with Pool, Yard & Patio

5.0
Outstanding (68 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 16 - Sep 23
$820 per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home in Marstons Mills with In-Ground Pool + Beautiful Views

5.0
Outstanding (61 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Oct 12 - Oct 19
-63%
$530
$198 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Cotuit with Grill, Patio & Yard + Sweeping Views

4.9
Outstanding (39 ratings)
Osterville, Barnstable, Massachusetts, United States
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Popular Rental Amenities in Osterville

  • Pet-friendly (212)
  • Air conditioning (694)
  • Pool (108)
  • WiFi (707)
  • No smoking (689)
  • TV (699)
  • Fireplace (364)
  • Washing machine (608)
  • Parking (54)
  • Kitchen (686)
  • Grill (609)
  • Microwave (625)

Our search page's filters will help you find the ideal vacation rental in Osterville. HomeToGo's data reveals that "Pets allowed" and "Air conditioning" prove to be the most frequently provided features in Osterville. You could even look for rentals if you'd like to have a fenced-in yard (57 rentals include "Fenced" in Osterville) or if you want to spend your vacation in privacy (5 rentals in Osterville include "Detached").

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 May
59°
57°

0%

4 h

10 mi/h

Wed, 22 May
64°
62°

0%

5 h

12 mi/h

Thu, 23 May
69°
60°

10%

4 h

13 mi/h

Fri, 24 May
73°
66°

10%

5 h

10 mi/h

Sat, 25 May
68°
59°

0%

2 h

8 mi/h

Sun, 26 May
60°
59°

0%

1 h

9 mi/h

Mon, 27 May
64°
62°

15%

0 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 $819 a night, with an average size of 228 m². Furthermore, these properties are perfect for 9 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 $536 per night for an area of 92 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 available 729 rentals
💳 Possible discounts up to 61%
🌙 Nightly prices starting at $150
⭐ Popular amenities Pets allowed, Air conditioning and Pool
🐾 Pet friendly homes 220 homes
🏊 Vacation rentals with pools 109 homes

Frequently Asked Questions

What is the typical price per night for a vacation home in Osterville?

The price of a night's stay in Osterville starts at $150. If you are looking for a house rental, the nightly price is $819 on average. A cabin Osterville will cost on average $536 per night.

How many vacation rentals are available to book in Osterville?

Currently there are 729 rentals in Osterville to choose from and rent for your upcoming trip.

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

Travelers search for Pets allowed, Air conditioning, and Pool when booking a vacation rental in Osterville.

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

There are 109 vacation rentals across 7 providers in Osterville.

Are pets allowed in vacation rentals in Osterville?

If traveling with a pet in Osterville, 30% of vacation rentals allow pets.

What are the best months to travel to Osterville?

When looking for a vacation rental in Osterville, consider that rainy season is typically in February or December, with August often being the driest.

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