Osterville Resorts
Cottage
10.0(61 Reviews)
2 Bedrooms
1 Bath
3 Guests
500 ft²
Oceanfront
Parking
Ocean View
Balcony/Terrace
US $410/Night
7 Nights - US $2,871
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
505.9 ft²
- Parking
- Balcony/Terrace
Internet
Child Friendly
US $390/Night
7 Nights - US $2,730
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $406/Night
7 Nights - US $2,840
House
9.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
1517.71 ft²
- Parking
- Balcony/Terrace
Air Conditioner- Internet
US $876/Night
7 Nights - US $6,129
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $539/Night
7 Nights - US $3,771
House
9.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
1926.74 ft²
- Parking
Pool- Balcony/Terrace
Kitchen
US $824/Night
7 Nights - US $5,768
House
10.0(1 Review)
3 Bedrooms
1 Bath
4 Guests
500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $465/Night
7 Nights - US $3,254
House
8.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1345.49 ft²
- Parking
- Pool
- Balcony/Terrace
View
US $420/Night
7 Nights - US $2,940
House
9.6(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Air Conditioner
- Internet
TV
US $472/Night
7 Nights - US $3,301
House
8.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
904.17 ft²
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
US $271/Night
7 Nights - US $1,897
Cottage
8.6(11 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $457/Night
7 Nights - US $3,202
House
1 Bedroom
1 Bath
10 Guests
2454.17 ft²
- Parking
- View
- Air Conditioner
- Internet
US $1,112/Night
7 Nights - US $7,785
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:
- The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views! RPMS104
- Impressive Osterville Residence - Ideal Location
- Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
- Osterville - close to town & beach, AC, beach pass
- Osterville Retreat – A/C, WiFi & Pet-Friendly
- Osterville pool rental near beach. Back yard paradise! RPMS138
- 5 minutes to beach, newly redone house w hot tub/screening room in osterville
- Osterville Retreat, Hot Tub, Beach Pass, 6 min from beach, 3 BR
- Cozy Getaway with Beach Pass & Sunroom
- Cape Cod getaway near Craigville Beach
2. How many Resorts are available in Osterville?
Currently, the total number of properties listed by RBO in 2026 is over 166 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
House
3 Bedrooms
2 Baths
6 Guests
1671 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $848/Night
7 Nights - US $5,933
House
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $430/Night
7 Nights - US $3,011
House
1 Bedroom
1 Bath
2 Guests
500 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $286/Night
7 Nights - US $2,002
House
10.0(89 Reviews)
4 Bedrooms
3 Baths
10 Guests
3300 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,181/Night
7 Nights - US $8,268
House
10.0(25 Reviews)
3 Bedrooms
2 Baths
8 Guests
2700 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $511/Night
7 Nights - US $3,578
House
10.0(18 Reviews)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $909/Night
7 Nights - US $6,361
House
10.0(6 Reviews)
8 Bedrooms
7 Baths
20 Guests
- Oceanfront
Hot Tub- Parking
- Ocean View
US $2,316/Night
7 Nights - US $16,215
House
10.0(4 Reviews)
4 Bedrooms
4 Baths
9 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $1,146/Night
7 Nights - US $8,020
House
10.0(3 Reviews)
4 Bedrooms
5 Baths
10 Guests
Private Pool- Hot Tub
- Pool
- Air Conditioner
US $5,017/Night
7 Nights - US $35,119
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,521/Night
7 Nights - US $10,645
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $956/Night
7 Nights - US $6,695
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
2171 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $454/Night
7 Nights - US $3,176
