Winchester Vacation Rentals & One Degree Stays Homes
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Luxury Places to Stay in Winchester
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Top-Rated Vacation Rentals with a Pool in Winchester
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Pet-Friendly Vacation Rentals in Winchester
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Large Vacation Homes & Villas in Winchester
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Winchester Rentals and Airbnb Homes Under $200
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Instantly Bookable Vacation Homes in Winchester
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Book a Last Minute Place to Stay in Winchester
About Winchester Vacation Rentals
There are more than 39 vacation rentals that are available in Winchester. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) 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 ODS property in Winchester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Winchester, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS 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 (ODSs), and other popular Airbnb-style properties in Winchester. Places to stay near Winchester are 776.55 ftยฒ on average, with prices averaging $320 a night.
OneDegreeStays makes it easy and safe to find and compare vacation rentals in Winchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Winchester
| Type | Count |
|---|---|
| Vacation Homes | 22 |
| Holiday Apartments | 6 |
| Cottages | 6 |
Use these Quick Filters to Find a Vacation Rental in Winchester
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โ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winchester.
Weather in Winchester, CT
View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.
Top Attractions Around Winchester, CT
OneDegreeStays offers a large selection of top attractions around Winchester. Research things to do on your vacation before you visit Winchester.
Other Places to Stay in Winchester, CT
Frequently Asked Questions About Winchester?
What are the top vacation 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 Vacation Rentals in Winchester:
- Our Cottage - Small in size, Big in character, On beautiful Highland Lake
- Family House On Highland Lake with Dock
- Newly renovated year-round LAKEFRONT rental on Highland Lake! Sleeps 8-9!
- Unique & extraordinary experience - renew your senses. Delightful waterfront!
- Lakefront Tranquility/Fishermans Delight
- The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
- Lakeridge Litchfield Resort Townhome Pool Tennis Skiing
- The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
- Enjoy a restful stay with fast internet, smart TV and the company of your pet.
- Charming 3-bedroom lakehouse in Winchester with WiFi and AC
Which vacation homes in Winchester are best for families?
If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:
- Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
- Beautiful Cottage on the Number One Lake in CT
- SPRING 2025! Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c & heat
How many onedegreestays vacation rentals are available in Winchester?
Currently, the total number of properties listed by One Degree Stays in 2025 is over 39 in the Winchester area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Winchester.โฏ
