1. USA
  2. Massachusetts
  3. Osterville
  4. Winter Rental

Osterville Winter Rentals & Holiday Homes

Discover winter rentals Osterville - We found 94 exact matches

About Osterville Winter Rental on BedroomVillas.com.au

At BedroomVillas, we feature a wide range of listings for accommodations in Osterville, MA that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and rent-by-owner homes, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.

BedroomVillas offers luxury finds for travelers planning on renting a place in Osterville, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Osterville and unlock even more amazing deals. Relax with BedroomVillas.

Show more
Show less

Frequently Asked Questions About Osterville Winter Rentals

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 Winter Rentals in Osterville:

The average cost for winter rentals in Osterville is $1,311 per night. BedroomVillas.com.au has a wide list of great winter places to stay near Osterville that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Osterville that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Osterville on BedroomVillas.com.au

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Osterville to find what works for you.
As of 2026, the data from BedroomVillas.com.au shows that there are over 94 private swimming pools or indoor pools accommodations near Osterville along with other great amenities.

About 94 holiday rentals in Osterville boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Osterville for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Osterville with all the best amenities for your next trip.