Holiday Rentals Winchester from £87: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Winchester has to offer?

Unique and secluded A frame home on 31 acres with hot tub. : This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday rentals

1. Griffis Game Hunting and/or Getaway

West Union

BRAD T.

includes taxes & fees

1 Sept - 2 Sept

2. Country Cabin in Amish Country

Peebles

Rodney C.

includes taxes & fees

1 Sept - 2 Sept

3. Hunter Lodge (Secluded in Amish Country and peaceful)

Peebles

kathy b.

includes taxes & fees

1 Sept - 2 Sept

Green Township

Abby M.

includes taxes & fees

1 Sept - 2 Sept

10. Glamping Cabin | Huge Window | Over a Creek

Green Township

Kristen W.

includes taxes & fees

1 Sept - 2 Sept

11. The Bear Den (Secluded in Amish Country and peaceful)

Peebles

Christy A.

includes taxes & fees

1 Sept - 2 Sept

12. Glamping Cabin | Huge Window | Tree House Feel

Green Township

"The property is very remote, secluded and quiet. It is a pet friendly property that our dog very much enjoyed. For hikers this is a great location. We were very unlucky with the weather, so no fire pit or BBQing due to torrential rain (no one can control that). Amenities are solid. It is glamping. There is a gas station approx. 10 minutes away that serves some solid breakfast…Portsmouth is about 45 minutes away for some dinner options."

Stuart

includes taxes & fees

1 Sept - 2 Sept

13. Cowboy Saloon Cabin

Hamersville

Jared

includes taxes & fees

1 Sept - 2 Sept

14. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout

Kenneth

includes taxes & fees

1 Sept - 2 Sept

15. Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

Hamersville

Atonenent R.

includes taxes & fees

2 Sept - 3 Sept

16. The Huntsmen

Hillsboro

Marcia

includes taxes & fees

8 Sept - 9 Sept

17. The White Stag

Hillsboro

Gavin D.

includes taxes & fees

1 Sept - 2 Sept

18. The Beach House

Hillsboro

Heidi R.

includes taxes & fees

2 Sept - 3 Sept

19. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Rome

includes taxes & fees

1 Sept - 2 Sept

20. The Outdoorsman

Hillsboro

Mindy

includes taxes & fees

3 Sept - 4 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Winchester Hotel Reviews

Peaceful cabin with spectacular river and scenic views.

10/10 Excellent

"Amazing spot with wonderful views. Very cozy and private."

Countryside Inn & Suites

8/10 Good

"We had a really pleasant stay and were very happy with our experience here. The hotel could use some additional repairs and updates, but it was great to see that improvements were actively underway, including painting the exterior, and some of the interior finishes had already been refreshed. Overall, the hotel was clean, the staff were friendly and welcoming, and we felt very comfortable during our stay. If we’re ever back in the area, we would definitely choose to stay here again."

Moon River Bed and Breakfast

10/10 Excellent

"We had a wonderful stay at Moon River Bed & Breakfast Inn in Maysville this July and couldn’t have been happier with the experience. The inn is beautiful, warm, and full of character—the kind of place that feels like part of the experience rather than simply somewhere to sleep. The hospitality was exceptional. We felt genuinely welcomed and well cared for throughout our stay, and the attention to detail made everything comfortable and relaxing. The location was also perfect for enjoying Maysville and the surrounding area. We travel to Maysville regularly, and Moon River was such a refreshing change from the typical hotel experience. It has the charm and personal touches that make you look forward to coming back at the end of the day. We thoroughly enjoyed our stay and would absolutely return. If you’re visiting Maysville and want somewhere memorable, comfortable, and welcoming, Moon River Bed & Breakfast Inn is an easy recommendation. Five stars!"

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as £87 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

Unique and secluded A frame home on 31 acres with hot tub.: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake and Ripley Lions Club Community Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates