Osterville Ski Chalets
House
10.0(11 Reviews)
4 Bedrooms
3 Baths
10 Guests
Private Pool
Oceanfront
Hot Tub
Fireplace/Heating
US $1,354/Night
7 Nights - US $9,475
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
505.9 ft²
- Fireplace/Heating
Balcony/Terrace
Parking
Internet
US $390/Night
7 Nights - US $2,730
Cottage
10.0(61 Reviews)
2 Bedrooms
1 Bath
3 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $410/Night
7 Nights - US $2,871
House
9.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
1506.95 ft²
- Fireplace/Heating
- Balcony/Terrace
Air Conditioner- Internet
US $876/Night
7 Nights - US $6,129
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $406/Night
7 Nights - US $2,840
House
9.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
1926.74 ft²
Pool- Balcony/Terrace
Kitchen- Parking
US $824/Night
7 Nights - US $5,768
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $539/Night
7 Nights - US $3,771
House
8.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
1345.49 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $420/Night
7 Nights - US $2,940
House
10.0(1 Review)
3 Bedrooms
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $380/Night
7 Nights - US $2,663
House
8.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
904.17 ft²
- Balcony/Terrace
- Parking
- Internet
Child Friendly
US $271/Night
7 Nights - US $1,897
House
9.4(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Air Conditioner
- Internet
TV
US $470/Night
7 Nights - US $3,293
House
1 Bedroom
1 Bath
10 Guests
2454.17 ft²
- Fireplace/Heating
- View
Pet Friendly- Parking
US $1,112/Night
7 Nights - US $7,785
Why Choose Rent By Owner for your Osterville Ski Chalets?
What makes our Ski Chalets 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 Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. 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 Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets 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 Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets 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 Ski Chalets in Osterville:
- 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
- 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
- Charming home with open layout, deck, grill, AC, W/D, & yard
- Osterville pool rental near beach. Back yard paradise! RPMS138
2. How many Ski Chalets are available in Osterville?
Currently, the total number of properties listed by RBO in 2026 is over 170 in the Osterville area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Osterville.
More Rentals You May Like Near Osterville
House
3 Bedrooms
2 Baths
6 Guests
1671 ft²
- Oceanfront
- Fireplace/Heating
- 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 $393/Night
7 Nights - US $2,754
House
1 Bedroom
1 Bath
2 Guests
500 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,010
House
10.0(88 Reviews)
4 Bedrooms
3 Baths
10 Guests
3300 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,185/Night
7 Nights - US $8,292
House
10.0(24 Reviews)
4 Bedrooms
2 Baths
8 Guests
2700 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $542/Night
7 Nights - US $3,795
House
10.0(19 Reviews)
5 Bedrooms
5 Baths
10 Guests
3000 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,181/Night
7 Nights - US $8,265
House
10.0(18 Reviews)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $942/Night
7 Nights - US $6,594
House
10.0(17 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $900/Night
7 Nights - US $6,300
House
10.0(14 Reviews)
4 Bedrooms
1 Bath
6 Guests
1650 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,462/Night
7 Nights - US $10,232
House
10.0(8 Reviews)
4 Bedrooms
4 Baths
12 Guests
3988 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,732/Night
7 Nights - US $19,126
House
10.0(4 Reviews)
8 Bedrooms
7 Baths
20 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $2,306/Night
7 Nights - US $16,143
House
10.0(4 Reviews)
4 Bedrooms
4 Baths
9 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $1,136/Night
7 Nights - US $7,954
