Winchester Holiday Rentals

Compare Villas, Resorts, & Rentals in Winchester, Elkton, Maryland, USA

New Cozy Cottage on the North East River in Town!
New
2 Bedrooms 6 Guests
From CA $178 per night
|
8.0 (88 Reviews)
14 Bedrooms 26 Guests
From CA $188 per night
8.8 (167 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
|
9.1 (8 Reviews)
10 Bedrooms 4 Guests
9.2 (964 Reviews)
1 Bedroom 2 Guests
10.0 (12 Reviews)
2 Bedrooms 8 Guests
From CA $233 per night
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8.8 (153 Reviews)
10 Bedrooms 22 Guests
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9.0 (1004 Reviews)
1 Bedroom 2 Guests
From CA $302 per night
10.0 (7 Reviews)
2 Bedrooms 5 Guests
|
8.6 (528 Reviews)
72 Bedrooms 19 Guests
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8.6 (223 Reviews)
111 Bedrooms 26 Guests
9.6 (4 Reviews)
1 Bedroom 6 Guests
|
8.6 (71 Reviews)
122 Bedrooms 26 Guests
8.6 (7 Reviews)
2 Bedrooms 4 Guests
8.3 (140 Reviews)
71 Bedrooms 20 Guests
From CA $219 per night
2.0 (1 Review)
2 Bedrooms 4 Guests
|
8.1 (132 Reviews)
80 Bedrooms 27 Guests
From CA $197 per night
New
2 Bedrooms 6 Guests
From CA $237 per night
|
7.7 (106 Reviews)
102 Bedrooms 16 Guests
10.0 (75 Reviews)
3 Bedrooms 6 Guests
From CA $147 per night
|
7.5 (207 Reviews)
75 Bedrooms 18 Guests
10.0 (23 Reviews)
3 Bedrooms 6 Guests
From CA $96 per night
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6.0 (194 Reviews)
127 Bedrooms 16 Guests
5.1 (89 Reviews)
30 Bedrooms 16 Guests
From CA $103 per night
5.1 (83 Reviews)
89 Bedrooms 10 Guests
10.0 (1 Review)
4 Bedrooms 8 Guests
From CA $96 per night
5.0 (4 Reviews)
10 Bedrooms 6 Guests
9.8 (40 Reviews)
3 Bedrooms 9 Guests
From CA $124 per night
New
114 Bedrooms 5 Guests
9.8 (8 Reviews)
3 Bedrooms 6 Guests
2.0 (1 Review)
3 Bedrooms 6 Guests
10.0 (14 Reviews)
4 Bedrooms 12 Guests
9.8 (79 Reviews)
5 Bedrooms 13 Guests
|
9.0 (525 Reviews)
1 Bedroom 2 Guests
From CA $163 per night
8.6 (694 Reviews)
1 Bedroom 2 Guests
8.4 (518 Reviews)
1 Bedroom 2 Guests
8.0 (911 Reviews)
1 Bedroom 2 Guests
|
8.0 (847 Reviews)
1 Bedroom 2 Guests
8.0 (9 Reviews)
1 Bedroom 2 Guests
From CA $151 per night
7.8 (599 Reviews)
1 Bedroom 2 Guests
From CA $116 per night
6.4 (448 Reviews)
1 Bedroom 2 Guests
From CA $108 per night
6.0 (1002 Reviews)
1 Bedroom 2 Guests
5.2 (464 Reviews)
1 Bedroom 2 Guests
From CA $97 per night
4.8 (40 Reviews)
1 Bedroom 2 Guests

About Casai's Private Villas and Holiday Rentals in Winchester

Discover more than 71 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 281.79 ft², with nightly prices averaging CA $307.

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.

Frequently Asked Questions About Winchester?

What are the top holiday rentals in Winchester?

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

As of 2025, Casai boasts over 71 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.