139+ Private Villas and Holiday Rentals in Winchester |
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  2. New Hampshire
  3. Winchester

Winchester Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winchester

Discover more than 139 vacation rentals available in Winchester. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winchester.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winchester, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winchester. On average, places to stay near Winchester offer 749.79 ft², with nightly prices averaging CA $363.

With Casai, finding and comparing holiday rentals in Winchester is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winchester

Type Count
Vacation Homes 47
Holiday Apartments 27
Cottages 8

Use these Quick Filters to Find a Holiday Rental in Winchester

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winchester.

Weather in Winchester, NH

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winchester, NH

Casai offers a large selection of top attractions around Winchester . Research things to do on your vacation before you visit Winchester.


Keene State College
Spofford Lake
Deerfield Academy
Greenfield Community College
Northfield Mount Hermon School
Brattleboro Bowl
Turner Falls
Bridge of Flowers
Landmark College
Magic Wings Butterfly Conservatory
Asbury United Methodist Church
The Putney School
Monadnock State Park
Brattleboro Outlet Center
Brattleboro Farmers' Market
Granite Gorge
Colonial Theatre
The Stone Church
Brattleboro Country Club

Other Places to Stay in Winchester, NH


Ashuelot 132 Properties

Frequently Asked Questions About Winchester?

What are the top holiday rentals in Winchester?

With numerous options available in Winchester, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winchester:

How many holiday rentals have private pools in Winchester?

Discover a selection of holiday rentals with private pools near Winchester with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Winchester are best for families?

If you're searching for a family-friendly holiday home in Winchester, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winchester:

How many Casai.ca holiday rentals are available in Winchester?

As of 2025, Casai boasts over 139 properties listed in the Winchester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winchester.


People Also Ask

There are 139 Winchester, NH Holiday Rentals

Recently Booked Holiday Rentals in Winchester