Winchester Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Winchester, Elkton, Maryland, USA

10.0 (3 Reviews)
1 Bedroom 2 Guests
From GB £97 per night
|
8.0 (88 Reviews)
14 Bedrooms 26 Guests
From GB £103 per night
8.8 (167 Reviews)
1 Bedroom 2 Guests
10.0 (12 Reviews)
2 Bedrooms 8 Guests
|
9.1 (8 Reviews)
10 Bedrooms 4 Guests
9.2 (964 Reviews)
1 Bedroom 2 Guests
From GB £165 per night
10.0 (7 Reviews)
2 Bedrooms 5 Guests
From GB £127 per night
|
8.8 (153 Reviews)
10 Bedrooms 22 Guests
|
9.0 (1004 Reviews)
1 Bedroom 2 Guests
|
8.7 (219 Reviews)
111 Bedrooms 26 Guests
10.0 (1 Review)
2 Bedrooms 6 Guests
From GB £104 per night
|
8.6 (528 Reviews)
72 Bedrooms 19 Guests
9.6 (4 Reviews)
1 Bedroom 6 Guests
|
8.5 (71 Reviews)
122 Bedrooms 26 Guests
From GB £111 per night
2.0 (1 Review)
1 Bedroom 4 Guests
8.3 (140 Reviews)
71 Bedrooms 20 Guests
From GB £108 per night
New
2 Bedrooms 6 Guests
|
8.1 (132 Reviews)
80 Bedrooms 27 Guests
10.0 (77 Reviews)
3 Bedrooms 6 Guests
From GB £129 per night
|
7.8 (105 Reviews)
67 Bedrooms 16 Guests
10.0 (25 Reviews)
3 Bedrooms 6 Guests
From GB £80 per night
|
7.6 (207 Reviews)
75 Bedrooms 18 Guests
From GB £53 per night
|
6.0 (194 Reviews)
127 Bedrooms 16 Guests
10.0 (1 Review)
4 Bedrooms 8 Guests
5.1 (89 Reviews)
30 Bedrooms 16 Guests
9.8 (41 Reviews)
3 Bedrooms 9 Guests
From GB £56 per night
5.1 (83 Reviews)
89 Bedrooms 10 Guests
9.8 (8 Reviews)
3 Bedrooms 6 Guests
From GB £53 per night
5.0 (4 Reviews)
10 Bedrooms 6 Guests
From GB £68 per night
4.0 (1 Review)
114 Bedrooms 5 Guests
10.0 (14 Reviews)
4 Bedrooms 12 Guests
9.8 (79 Reviews)
5 Bedrooms 13 Guests
New Charming 3rd floor Large bedroom inside townhome
New
1 Bedroom 2 Guests
New Room #4 in Elkton, MD – Easy Access to I-95
New
1 Bedroom 2 Guests
New Room #3 in Elkton, MD – Easy Access to I-95
New
1 Bedroom 4 Guests
|
9.0 (527 Reviews)
1 Bedroom 2 Guests
From GB £89 per night
8.6 (694 Reviews)
1 Bedroom 2 Guests
8.4 (521 Reviews)
1 Bedroom 2 Guests
8.0 (940 Reviews)
1 Bedroom 2 Guests
|
8.0 (847 Reviews)
1 Bedroom 2 Guests
8.0 (12 Reviews)
1 Bedroom 2 Guests
From GB £82 per night
7.8 (599 Reviews)
1 Bedroom 2 Guests
From GB £63 per night
6.4 (448 Reviews)
1 Bedroom 2 Guests
From GB £54 per night
6.0 (1005 Reviews)
1 Bedroom 2 Guests
From GB £53 per night
5.6 (50 Reviews)
1 Bedroom 2 Guests
5.2 (481 Reviews)
1 Bedroom 2 Guests

About Winchester Vacation Rentals

With more than 74 Winchester 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 Winchester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Winchester, 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 Winchester. Places to stay near Winchester are 309.12 ft² on average, with prices averaging GB £156 a night.

RentByOwner 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.

Frequently Asked Questions About Winchester?

What are the top vacation rentals in Winchester?

How many Rentbyowner vacation rentals are available in Winchester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 74 in the Winchester 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 Winchester.