Best Vacation Homes in Osterville
New
House
3 Bedrooms
2 Baths
6 Guests
1288 ft²
Oceanfront
Fireplace/Heating
Ocean View
View
£536/Night
7 Nights - £3,755
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
505.9 ft²
- Fireplace/Heating
Balcony/Terrace
Parking
Internet
£226/Night
7 Nights - £1,582
Cottage
10.0(61 Reviews)
2 Bedrooms
1 Bath
3 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£246/Night
7 Nights - £1,722
House
9.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
1506.95 ft²
- Fireplace/Heating
- Balcony/Terrace
Air Conditioner- Internet
£653/Night
7 Nights - £4,571
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£356/Night
7 Nights - £2,489
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£368/Night
7 Nights - £2,577
House
10.0(1 Review)
3 Bedrooms
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
£284/Night
7 Nights - £1,986
House
9.4(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Air Conditioner
- Internet
TV
£340/Night
7 Nights - £2,379
Osterville Luxury Rentals
House
6 Bedrooms
7 Baths
22 Guests
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
£4,322/Night
7 Nights - £30,256
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
Pool
£4,180/Night
7 Nights - £29,262
House
6 Bedrooms
7 Baths
12 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£3,636/Night
7 Nights - £25,449
House
9.8(35 Reviews)
7 Bedrooms
7 Baths
10 Guests
7000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£3,518/Night
7 Nights - £24,625
House
10.0(1 Review)
6 Bedrooms
5 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£3,489/Night
7 Nights - £24,425
House
10.0(3 Reviews)
4 Bedrooms
5 Baths
10 Guests
- Private Pool
- Hot Tub
- Pool
Pet Friendly
£3,476/Night
7 Nights - £24,331
House
9.2(9 Reviews)
11 Bedrooms
7 Baths
22 Guests
7400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£2,600/Night
7 Nights - £18,201
House
5 Bedrooms
6 Baths
18 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£2,372/Night
7 Nights - £16,606
Osterville Pet Friendly Vacation Rentals
House
3 Bedrooms
2 Baths
6 Guests
1671 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£632/Night
7 Nights - £4,425
House
1 Bedroom
1 Bath
10 Guests
2454.17 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
£829/Night
7 Nights - £5,806
House
10.0(17 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£591/Night
7 Nights - £4,140
House
4 Bedrooms
2 Baths
8 Guests
3390.63 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
£748/Night
7 Nights - £5,235
House
10.0(4 Reviews)
8 Bedrooms
7 Baths
20 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£2,337/Night
7 Nights - £16,357
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£1,010/Night
7 Nights - £7,067
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£713/Night
7 Nights - £4,993
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£607/Night
7 Nights - £4,251
Osterville Large Vacation Homes
House
10.0(88 Reviews)
4 Bedrooms
3 Baths
10 Guests
3300 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£775/Night
7 Nights - £5,427
House
9.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
1926.74 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
£615/Night
7 Nights - £4,302
House
10.0(19 Reviews)
5 Bedrooms
5 Baths
10 Guests
3000 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£882/Night
7 Nights - £6,177
House
10.0(8 Reviews)
4 Bedrooms
4 Baths
12 Guests
3988 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£2,106/Night
7 Nights - £14,739
House
10.0(2 Reviews)
6 Bedrooms
5 Baths
15 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
£1,152/Night
7 Nights - £8,066
House
10.0(1 Review)
5 Bedrooms
4 Baths
12 Guests
2758 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£1,001/Night
7 Nights - £7,009
House
9.8(45 Reviews)
4 Bedrooms
3 Baths
11 Guests
3700 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£1,441/Night
7 Nights - £10,089
House
9.8(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
2900 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£1,017/Night
7 Nights - £7,118
Why Choose Rent By Owner for your Osterville Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Osterville
When should you plan your Vacation Rentals stay?
Choosing the best time to vacation here ensures you experience the area's natural beauty and relaxing atmosphere at its peak, making your stay in Osterville, Massachusetts, truly memorable.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, ideal for relaxing seaside activities in this coastal area.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Early Fall (September to October)
The early fall offers pleasant temperatures and fewer crowds, making it a perfect time to explore and unwind in this charming destination.
Average Temperature Daytime: 68°F to 77°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Late Fall to Winter (November to February)
During these months, expect cooler weather with fewer visitors, providing a peaceful atmosphere for those seeking solitude and quiet exploration.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Early Spring (March to May)
As the region transitions into spring, the area begins to awaken with mild temperatures, offering a serene setting before the busy summer season begins.
Average Temperature Daytime: 50°F to 65°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Osterville
How to Book Your Osterville Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Osterville
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck for relaxing and dining al fresco amid the scenery.
- Take advantage of lush, landscaped gardens that enhance your outdoor experience in this coastal region.
- Make the most of a spacious yard perfect for outdoor games and family gatherings during your stay.
- Utilize outdoor grilling equipment to savor delicious meals with views of the surrounding area.
- Explore nearby pathways or trails for walking, jogging, or biking through the scenic landscape.
- Relax at a private swimming pool or hot tub available at select properties in this seaside destination.
- Capitalize on waterfront access or proximity for activities like kayaking, paddleboarding, or fishing while here.
Top Attractions Around Osterville
What attractions are nearby?
Within this charming region, you'll find a variety of outdoor activities and scenic spots to explore, offering a perfect blend of relaxation and adventure during your stay.
Family Activities
- Dowses Beach: Spend a day at this family-friendly beach, where you can relax on the sandy shores and enjoy safe swimming within calm waters.
- Wianno Golf Course: Experience a fun round of golf suitable for all ages, set amidst scenic views that capture the region's charming coastal atmosphere.
- Osterville Historical Museum: Discover local history through engaging exhibits that offer educational fun for children and adults alike in this inviting community setting.
- Barnstable County Fairgrounds: Attend seasonal fairs, festivals, and outdoor events that bring families together for entertainment and local cultural experiences.
Adult Activities
- Fishing Charters: Enjoy a day on the water with guided fishing trips that allow you to experience the region's rich maritime heritage firsthand.
- Harbor Cruises: Explore the scenic coastline and learn about local history on a relaxing harbor cruise, perfect for unwinding in this seaside destination.
- Golfing: Tee off at nearby golf courses offering picturesque views and challenging holes, ideal for adding some leisure to your stay here.
- Wildlife Watching: Discover diverse bird species and marine life in the area’s protected nature reserves, providing memorable experiences for nature enthusiasts.
Other Places to Stay in Osterville, MA
Dowses Beach
Stand Up & Paddle Cape Cod
Public Beach
Wianno
Osterville Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit During the Off-Peak Seasons: Visiting outside of peak summer months can help you enjoy a more relaxed atmosphere and better rates at your vacation rental here.
- Explore Local Waterfront Activities: Take advantage of the region's scenic waterways by engaging in boating, kayaking, or fishing to fully experience the area's natural beauty.
- Discover Nearby Dining and Shopping Spots: Supporting local eateries and boutiques enhances your stay and offers a more authentic experience of this destination.
- Book Well in Advance: Secure your preferred vacation rental early to access the best properties and ensure availability during your planned travel dates.
Transportation Options
- Boston Logan International Airport: You can arrive at this major airport, just a short drive from the area, for convenient access to your vacation rentals.
- Cape Cod Transit Service: This regional bus service offers reliable transportation around Cape Cod, making it easy to explore nearby towns and beaches.
- Local Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available within the region, providing flexible transportation during your stay.
- Private Car Rentals: Renting a car locally grants you the freedom to discover all the scenic spots and hidden gems here at your own pace.
Local Customs Options
- Community Events and Parades: Participating in local community events and parades is a cherished tradition here, offering an authentic glimpse into the area's close-knit spirit.
- Cape Cod Souvenirs and Crafts: Supporting local artisans by purchasing handmade crafts and souvenirs helps preserve the region’s artisanal heritage.
- Seafood Dining Etiquette: Enjoying fresh seafood often involves specific dining customs, reflecting the area's maritime roots and culinary traditions.
- Respect for Marine Conservation: Visitors are encouraged to observe eco-friendly practices and show respect for marine life, emphasizing the region's commitment to preserving its natural beauty.
Frequently Asked Questions About Osterville?
1. What are the top vacation rentals in Osterville?
There are a lot of options in Osterville. If you plan on staying in the Osterville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Osterville:
- BEAUTIFUL and PRIVATE OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING
- Charming Cottage Getaway
- Lovely Osterville Home With New Gunite Pool and Beach Pass.
- Osterville~Newly Renovated with central AC and beach pass
- Osterville Cape Cod-Style Home - One Block from North Bay!
- Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.
- Beach pass included Modern 3BR Osterville retreat, walkable to village center
- "The Half Shell" Cottage in Osterville Village
- 4BR 4BA Osterville home with pool, hot tub, game room-minutes from the beach!
- Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
2. How many vacation rentals have private pools in Osterville?
There are 23 vacation rentals with private pools near Osterville. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Osterville are best for families?
If you are looking for a family-friendly vacation home in Osterville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osterville:
4. How many Rentbyowner vacation rentals are available in Osterville?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 172 in the Osterville area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Osterville.
5. What is the cancellation policy for vacation rentals in Osterville, Massachusetts?
Cancellation policies vary depending on the specific listing. You should review the cancellation terms listed for each property or contact the owner directly to understand your options and any potential fees.
6. How do I verify the safety and cleanliness standards of a vacation rental here?
Safety and cleanliness standards are typically detailed in the listing description. You can also reach out to the property owner for additional information to ensure the property meets your expectations for a secure stay.
7. Are there any special amenities or features included with vacation rentals in this destination?
Amenities vary across properties, from private pools to outdoor spaces. To find accommodations that suit your needs, review the listing details or contact the owner for specific amenities available during your stay.
8. What are the check-in and check-out procedures for rentals in this region?
Check-in and check-out times are specified in each listing. For any special requests or detailed procedures, it’s best to communicate directly with the property owner before your arrival.
9. Is there support available if I encounter issues during my stay in a vacation rental here?
Support options depend on the individual rental. Most listings offer contact information for the owner or local support services, so reaching out directly ensures a prompt resolution to any concerns during your visit.
Osterville Top Rated Vacation Rentals
House
10.0(31 Reviews)
4 Bedrooms
3 Baths
8 Guests
3500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£1,451/Night
7 Nights - £10,158
House
10.0(14 Reviews)
4 Bedrooms
1 Bath
6 Guests
1650 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£1,018/Night
7 Nights - £7,127
House
9.6(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
1344 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£727/Night
7 Nights - £5,090
House
Waterfront Estate in Prestigious Osterville | Private Beach, Pool & Hot Tub and Central AC-Sleeps 15
9.0(2 Reviews)
6 Bedrooms
5 Baths
15 Guests
4470 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£2,018/Night
7 Nights - £14,128
House
8.0(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
1930 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£411/Night
7 Nights - £2,874
House
8.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
1345.49 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
£313/Night
7 Nights - £2,193
House
5 Bedrooms
4 Baths
10 Guests
3800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£1,609/Night
7 Nights - £11,265
House
4 Bedrooms
2 Baths
8 Guests
3387 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£617/Night
7 Nights - £4,319
