Winchester Holiday Rentals from €53: Search Short-Term Rentals

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

Unique waterside home in stunning location. : This holiday home rental outside of Winchester is located on the waterfront, and has a balcony, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Our top choices for Winchester holiday rentals

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

1. Settle Winchester

Winchester City Center

includes taxes & fees

8 Nov - 9 Nov

A modern interior with a staircase, seating area, and a green wall.

2. Winchester Wessex Hotel by Sunday Twin Room

Winchester City Center

Hayden

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a skylight, a bed, a dresser, a sofa, and a view of the garden through a sliding door.

3. Garden room, central Winchester – self-contained, kitchenette & parking

Winchester

includes taxes & fees

8 Nov - 9 Nov

A bed with a teal headboard, two pillows with tropical leaf patterns, and two folded towels on a yellow bedspread.

4. Winchester City Centre Flat/Sleeps 6/Free Parking

Hampshire

includes taxes & fees

29 Nov - 30 Nov

A neatly made bed with a grey quilt, two pillows, and rolled towels on the side. There is a bedside table with a lamp and a small decorative item.

5. Aethelred Annexe - New Build with Full Amenities

Winchester

Andrea W.

A wooden cabin with a sloped roof, a deck with two chairs, and a glass door leading inside.

6. Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Winchester

Nicola H.

includes taxes & fees

8 Nov - 9 Nov

A modern interior with a red sofa, black chairs, and a patterned floor.

7. Second Nature Southampton

Southampton City Centre

Gary

includes taxes & fees

13 Nov - 14 Nov

A historic building with a paved entrance and a stone structure with a red door.

8. Beddoe Apartments

Eastleigh

Alan

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

9. Settle Southampton

Freemantle

Chris

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a large bed, a nightstand, a wall-mounted lamp, and a window with blinds.

10. Southampton Serviced Apartment

Bassett

Emma

includes taxes & fees

2 Dec - 3 Dec

A green RV with a fire pit and outdoor seating area, surrounded by lanterns and plants.

11. The Shack Cabin Sleeps 3 With Enclosed Garden

Waterlooville

includes taxes & fees

19 Nov - 20 Nov

A tent with a bed inside, a colorful rug, and a sign on the ground.

12. Stone Circle Glamping

Durrington

Darnell

includes taxes & fees

2 Dec - 3 Dec

A dining area with a view of a swimming pool, a table with food, and a chair.

13. Beam Cottage

Southampton

includes taxes & fees

17 Nov - 18 Nov

A dining table set with plates, cutlery, and wine glasses, surrounded by woven placemats and a vase with yellow flowers.

14. 3 Bedrooms house ideal for long Stays!

Southampton

Michael R.

includes taxes & fees

29 Nov - 30 Nov

A bedroom with a wooden headboard, white bedding, two floral pillows, a bedside lamp, and a folded towel on the bed.

15. The Riley Stable- Cozy Getaway

Waterlooville

includes taxes & fees

8 Nov - 9 Nov

A wooden cabin with an open door, surrounded by lush greenery.

16. Cosy Wigwam Holidays Cabin With Ensuite

Chawton

NASTASSIA N.

includes taxes & fees

7 Nov - 8 Nov

A bedroom with a bed, a chair, a TV, and a window.

17. Orchard Road

Southsea

includes taxes & fees

7 Nov - 8 Nov

A historic building with timber framing, a stone facade, and a covered passageway with purple wisteria.

18. Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Stockbridge

Grace O.

A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

19. Charles Hope Salisbury Centre

Salisbury

Theodros

includes taxes & fees

15 Nov - 16 Nov

20. The South Coast Snug

Fareham

Nikki

includes taxes & fees

9 Nov - 10 Nov

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Find holiday rentals that suit your style

Top Winchester Hotel Reviews

A brick building with a sign for 'The White Star' dining, bar, and rooms.

The White Star Tavern

Southampton City Centre

10/10 Excellent

Clive

A brick house with a garden in front, a gate, and a lamp post.

The Montagu Arms Hotel

Brockenhurst

8/10 Good

marc

A brick pathway leading to a building with a sign reading "Hotel du Vin & Bistro Garden Rooms."

Hotel du Vin & Bistro Winchester

Winchester City Center

10/10 Excellent

Donald

A two-story building with a patio area featuring outdoor seating and planters.

The White Horse Hotel, Romsey, Hampshire

Romsey

10/10 Excellent

KATHRYN

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 €53 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 in Winchester close to Winchester Science Centre and Planetarium, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the stunning cathedral and picturesque gardens in Winchester. The array of shops and festivals are some other things you might want to check out while you're here.

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

Unique waterside home in stunning location.: This holiday home rental outside of Winchester is located on the waterfront, and has a balcony, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winchester?

Expedia has 37 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Winchester Science Centre and Planetarium and Marwell Zoo are a couple of the family-friendly sights, whereas cultural attractions include Great Hall and Theatre Royal Winchester. While in the area, you can also visit popular places such as Southampton Cruise Terminal and New Forest National Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.

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Things to do in Winchester
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Holiday Rentals in Winchester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester holiday rentals

1. Settle Winchester

2. Winchester Wessex Hotel by Sunday Twin Room

3. Garden room, central Winchester – self-contained, kitchenette & parking

4. Winchester City Centre Flat/Sleeps 6/Free Parking

5. Aethelred Annexe - New Build with Full Amenities

6. Cosy A-Frame cabin nestled in the chalk steams of Hampshire

7. Second Nature Southampton

8. Beddoe Apartments

9. Settle Southampton

10. Southampton Serviced Apartment

11. The Shack Cabin Sleeps 3 With Enclosed Garden

12. Stone Circle Glamping

13. Beam Cottage

14. 3 Bedrooms house ideal for long Stays!

15. The Riley Stable- Cozy Getaway

16. Cosy Wigwam Holidays Cabin With Ensuite

17. Orchard Road

18. Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

19. Charles Hope Salisbury Centre

20. The South Coast Snug

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

The White Star Tavern

10/10 Excellent

Find out more about Winchester

Winchester holiday rentals: An excellent choice for every season

How to find incredible deals on Winchester rentals

Frequently Asked Questions

Can I find holiday rentals in Winchester?

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

How many holiday rentals are there in Winchester?

What’s there to see and do in Winchester?

What’s a holiday rental in Winchester like?

Explore a world of travel with Expedia