What are the top rated Summer Rentals in Winchester?

There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Winchester: Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood. Heavenly Bungalow, immaculately clean, close to downtown! Historical John Rast House Riverfront Log Cabin in Roseburg’s Wine Country Luxury, Full Service Bed and Breakfast - you are the only guest in our home! Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI The Mable LUXE - Calming Retreat - Entire Home Singing Waters at N. Umpqua Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants Dreamy Hilltop View: Roseburg Wine Country Retreat

How many summer rentals are available around Winchester, OR?

In 2025, Casai offers 48 summer rentals in or around Winchester. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

How much does it cost to rent a summer rental in Winchester?

The average price per night for a summer rental in Winchester is $231 . Check the full list of summer accommodations in Winchester.

How many summer rentals are available to book in Winchester?

There are 48 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.ca.

Do any summer rentals in Winchester have a private pool?

Yes, here are some popular summer holiday rentals in Winchester that have a private or indoor pool: Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood. Terraluna Inn Historical John Rast House Heavenly Bungalow, immaculately clean, close to downtown! Check all holiday rentals with a pool in Winchester on Casai.ca.

Can I rent pet-friendly summer rentals in Winchester?

Yes, We have 48 summer rental homes in Winchester and types of place to stay in Winchester include: Vacation Homes: 48 available for rent Villas: 48 Rentals available for rent Holiday Apartments: 48 Rentals available for rent Hotels with Suites: 48 Rentals available for book

Do you have a luxury summer rental with a pool in Winchester?

Yes, of course! There are many luxury summer rental properties in Winchester. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Winchester.