Osterville Resorts
18 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,181/Night
For 7 Nights US $22,267
495.14 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Parking
- Internet
US $303/Night
For 7 Nights US $2,121
2450 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,620/Night
For 7 Nights US $11,338
1506.95 ft²
6 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Child Friendly
US $876/Night
For 7 Nights US $6,129
500 ft²
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $330/Night
For 7 Nights US $2,309
US $824/Night
For 7 Nights US $5,768
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $508/Night
For 7 Nights US $3,553
1345.49 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $420/Night
For 7 Nights US $2,940
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
US $494/Night
For 7 Nights US $3,455
904.17 ft²
5 Guests
2 Bedrooms
1 Bathroom
House
- Parking
- Internet
- Child Friendly
US $271/Night
For 7 Nights US $1,897
500 ft²
4 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $380/Night
For 7 Nights US $2,663
3390.63 ft²
8 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pool
- View
US $1,003/Night
For 7 Nights US $7,019
Why Choose Rent By Owner for your Osterville Resorts?
What makes our Resorts 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.
Weekly Weather Forecast for Osterville
How to Book Your Osterville Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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
Other Places to Stay in Osterville, MA
Dowses Beach
Stand Up & Paddle Cape Cod
Public Beach
Wianno
Osterville Resorts Frequently Asked Questions
1. What are the top Resorts 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 Resorts in Osterville:
- 4BR 4BA Osterville home with pool, hot tub, game room-minutes from the beach!
- Unbeatable location, views and private beach from this rare family compound
- New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
- Sea View Ave Brand New Construction - Pool Hot tub Tennis Court
- Charming Carriage House on Private Oceanfront Estate
- In the Heart of Osterville Village, Newly renovated, Pets considered RPMS087
- The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views! RPMS104
- Osterville - close to town & beach, AC, beach pass
- Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
- Osterville Retreat – A/C, WiFi & Pet-Friendly
2. How many Resorts are available in Osterville?
Currently, the total number of properties listed by RBO in 2026 is over 167 in the Osterville area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Osterville.
More Rentals You May Like Near Osterville
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
US $455/Night
For 7 Nights US $3,185
900 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $380/Night
For 7 Nights US $2,663
1671 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $791/Night
For 7 Nights US $5,535
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $381/Night
For 7 Nights US $2,664
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $180/Night
For 7 Nights US $1,260
3300 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,016/Night
For 7 Nights US $7,110
3500 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,974/Night
For 7 Nights US $13,820
2700 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $384/Night
For 7 Nights US $2,691
3000 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $818/Night
For 7 Nights US $5,728
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $793/Night
For 7 Nights US $5,551
1500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $602/Night
For 7 Nights US $4,217
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,379/Night
For 7 Nights US $9,656
