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Osterville Vacation Rentals

Find 558 available offers from 5 partners
Osterville
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Rating
4.5+
4+

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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Best Vacation Home Deals in Osterville

Save up to 63%

Cottage Osterville
Jan 6 - Jan 13
-54%
$250
$115 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Luxurious Cottage in Centerville with Grill

5.0
Outstanding (2 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Dec 16 - Dec 23
-63%
$1,143
$426 per night
House ∙ 24 guests ∙ 7 bedrooms

Wonderful House in Barnstable with Grill

5.0
Outstanding (1 rating)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Jan 20 - Jan 27
-38%
$982
$604 per night
House ∙ 16 guests ∙ 7 bedrooms

Vacation Home in Cotuit with Yard & Grill

4.5
Excellent (11 ratings)
Osterville, Barnstable, Massachusetts, United States
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Find a dreamlike accommodation from $95 per night by searching and comparing the 558 properties listed in Osterville. Each of the properties from our partner websites are directly compared by our algorithm to help you save up to 63%.

Top-Rated Rentals and Accommodations in Osterville

Book Vacation Rental Offers with the Highest User Rating

House Osterville
Jan 20 - Jan 27
$850 per night
House ∙ 10 guests ∙ 5 bedrooms

Family Friendly Lovely House in Popponesset with Grill & Yard

5.0
Outstanding (23 ratings)
Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Jan 6 - Jan 13
$277 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Great Cottage in Centerville with Yard & Grill + Water View

4.6
Excellent (18 ratings)
Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Mar 1 - Mar 8
-54%
$348
$160 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Beautiful Cottage in Marstons Mills with Yard & Grill

5.0
Outstanding (2 ratings)
Osterville, Barnstable, Massachusetts, United States
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Recommended Vacation Rentals in Osterville

Find your perfect vacation rental in Osterville: from $95 per night

House Osterville
Aug 3 - Aug 10
$397 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Centerville with Yard & Grill

Osterville, Barnstable, Massachusetts, United States
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Cottage Osterville
Jun 8 - Jun 15
$277 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Large Cottage in Centerville with Grill & Yard + Water Views

4.0
Very good (10 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Dec 9 - Dec 16
-73%
$401
$109 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Marstons Mills with Grill & Yard

4.7
Excellent (11 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Jan 6 - Jan 13
$497 per night
House ∙ 8 guests ∙ 3 bedrooms

Charming House in Centerville with Grill, Pool & Yard

4.5
Excellent (18 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Jun 15 - Jun 22
-27%
$745
$547 per night
House ∙ 8 guests ∙ 3 bedrooms

Fantastic House in Centerville with On-Site Parking

4.7
Excellent (63 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Sep 21 - Sep 28
-29%
$999
$709 per night
House ∙ 12 guests ∙ 5 bedrooms

Charming House in Sandwich with Gorgeous Pool

5.0
Outstanding (2 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Dec 6 - Dec 13
$335 per night
House ∙ 8 guests ∙ 4 bedrooms

Family Friendly House in Sandwich with Double Fireplace

5.0
Outstanding (7 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Dec 9 - Dec 16
-33%
$300
$200 per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home in Mashpee with Yard & Grill

4.6
Excellent (17 ratings)
Osterville, Barnstable, Massachusetts, United States
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Condo Osterville
Dec 9 - Dec 16
-36%
$238
$152 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Wonderful Condo in Marstons Mills with Yard

4.8
Outstanding (43 ratings)
Osterville, Barnstable, Massachusetts, United States
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Budget-friendly Vacation Rentals in Osterville

Find Fantastic yet Inexpensive Offers

Cottage Osterville
Jan 5 - Jan 12
$547 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

Cottage in Centerville with Yard & Grill + Beach View

4.8
Outstanding (40 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Jan 20 - Jan 27
-24%
$850
$646 per night
House ∙ 12 guests ∙ 4 bedrooms

Beautiful Vacation Home in Popponesset with Grill

5.0
Outstanding (47 ratings)
Osterville, Barnstable, Massachusetts, United States
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House Osterville
Jan 6 - Jan 13
-45%
$314
$174 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Osterville with Free Parking

4.6
Excellent (14 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.

House  Osterville
Jun 8 - Jun 15
-20%
$250
$200 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Hyannis with Yard & Grill

4.8
Outstanding (44 ratings)
Osterville, Barnstable, Massachusetts, United States
Air conditioning
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House  Osterville
Mar 9 - Mar 16
-37%
$497
$315 per night
House ∙ 2 guests ∙ 1 bedroom

House in East Sandwich with Grill

Osterville, Barnstable, Massachusetts, United States
Air conditioning
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House  Osterville
Jan 6 - Jan 13
-60%
$309
$125 per night
House ∙ 10 guests ∙ 4 bedrooms

Nice House in East Sandwich with Grill & Yard

3.7
Good (34 ratings)
Osterville, Barnstable, Massachusetts, United States
Air conditioning
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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
Jan 20 - Jan 27
-25%
$795
$595 per night
House ∙ 10 guests ∙ 4 bedrooms

Nice House in Centerville with Yard & Grill

5.0
Outstanding (33 ratings)
Osterville, Barnstable, Massachusetts, United States
Balcony
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House  Osterville
Jan 20 - Jan 27
$1,591 per night
House ∙ 16 guests ∙ 6 bedrooms

Nice House in Cotuit with Pool & Grill + Beautiful Views + Beach Nearby

4.8
Outstanding (37 ratings)
Osterville, Barnstable, Massachusetts, United States
Balcony
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House  Osterville
Jan 6 - Jan 13
-25%
$661
$497 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in New Seabury with Grill & Yard + Water Views + Beach Nearby

5.0
Outstanding (25 ratings)
Osterville, Barnstable, Massachusetts, United States
Balcony
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Osterville by booking a vacation home with a fireplace.

House  Osterville
Jan 20 - Jan 27
$597 per night
House ∙ 10 guests ∙ 4 bedrooms

Nice House in Centerville with Private Pool

4.1
Very good (50 ratings)
Osterville, Barnstable, Massachusetts, United States
Fireplace
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Cottage  Osterville
May 11 - May 18
-15%
$258
$219 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Centerville with Grill & Yard

5.0
Outstanding (58 ratings)
Osterville, Barnstable, Massachusetts, United States
Fireplace
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House  Osterville
Dec 8 - Dec 15
-69%
$448
$137 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Hyannis with Grill & Yard

4.1
Very good (12 ratings)
Osterville, Barnstable, Massachusetts, United States
Fireplace
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Popular Rental Amenities in Osterville

  • Pet-friendly (152)
  • Air conditioning (553)
  • Pool (88)
  • WiFi (576)
  • No smoking (486)
  • TV (565)
  • Fireplace (304)
  • Washing machine (478)
  • Parking (40)
  • Kitchen (543)
  • Grill (494)
  • Microwave (509)

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 want a rental with a jacuzzi (20 rentals include "Hot tub" in Osterville) or if you'd like to have a fenced-in yard (44 rentals in Osterville include "Fenced").

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

Wed, 6 Dec
37°
35°

50%

0 h

13 mi/h

Thu, 7 Dec
33°
32°

0%

4 h

5 mi/h

Fri, 8 Dec
44°
41°

10%

1 h

3 mi/h

Sat, 9 Dec
51°
46°

15%

3 h

1 mi/h

Sun, 10 Dec
55°
53°

15%

2 h

13 mi/h

Mon, 11 Dec
44°
44°

0%

3 h

9 mi/h

Tue, 12 Dec
42°
42°

0%

6 h

11 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 $838 a night, with an average size of 218 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 $539 per night for an area of 96 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 558 homes
💳 Possible discounts up to 63%
🌙 Nightly prices starting at $95
⭐ Popular amenities Pets allowed, Air conditioning and Pool
🐾 Pet friendly homes 146 homes
🏊 Vacation rentals with pools 87 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 $95. If you are looking for a house rental, the nightly price is $838 on average. A cabin Osterville will cost on average $539 per night.

How many vacation rentals are available to book in Osterville?

Currently there are 558 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 87 vacation rentals across 5 providers in Osterville.

Are pets allowed in vacation rentals in Osterville?

If traveling with a pet in Osterville, 26% 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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