Compare Vacation Rentals & Rent By Owner Homes in Winter Pond, Winchester, Massachusetts, USA
About Winter Pond Vacation Rentals
With more than 84 Winter Pond vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Winter Pond.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Winter Pond, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Winter Pond. Places to stay near Winter Pond are 433.08 ft² on average, with prices averaging US $373 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Winter Pond with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Winter Pond?
What are the top vacation rentals in Winter Pond?
- A charming modern suburban 3 bedroom condo close to Boston
- Located north of Boston/comfort and relaxation in your home away from home
- Deluxe and Bright 3Br, King Bed,W/D,Parking
- Enchanting Hidden Door Escape
- Funky and cozy home ! A little bit of everything for everyone.
- Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching
- Charming 1 BR private entrance apt commuters dream
- Stylish Studio - Sanitized , Private, Spotless
- Unique Cathedral Ceiling Condo W/D, Parking
- Modern Studio-Private Entrance,Washer+Dryer
How many Rentbyowner vacation rentals are available in Winter Pond?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 84 in the Winter Pond 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 Winter Pond.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Downtown Boston Vacation Rentals in Boston, Massachusetts | 183 |
| Back Bay Vacation Rentals in Boston, Massachusetts | 140 |
| Dorchester Vacation Rentals in Boston, Massachusetts | 50 |
| Fenway–Kenmore Vacation Rentals in Boston, Massachusetts | 47 |
| Seaport District Vacation Rentals in Boston, Massachusetts | 34 |
| Beacon Hill Vacation Rentals in Boston, Massachusetts | 30 |
| East Boston Vacation Rentals in Boston, Massachusetts | 271 |
| North End Vacation Rentals in Boston, Massachusetts | 605 |
| South Boston Vacation Rentals in Boston, Massachusetts | 1418 |
| Allston Vacation Rentals in Boston, Massachusetts | 418 |
| Jamaica Plain Vacation Rentals in Boston, Massachusetts | 312 |
| Charlestown Vacation Rentals in Boston, Massachusetts | 1671 |
