Winchester Vacation Rentals from ￥7,852: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Winchester?

Unique waterside home in stunning location. : This vacation 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 you can cook with friends or family.

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Our top choices for Winchester vacation rentals

A bedroom with a bed, a bedside table, a window, and a view of the outside.

1. Settle Winchester

Winchester City Center

￥20,846 total

includes taxes & fees

Nov 19 - Nov 20

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

2. Winchester Wessex Hotel by Sunday Twin Room

Winchester City Center

Hayden

￥18,793 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Winchester

Nicola H.

￥31,425 total

includes taxes & fees

Nov 15 - Nov 16

A brick house with a dark door, a small porch, and a potted plant.

4. Aethelred Annexe - New Build with Full Amenities

Winchester

Andrea W.

￥21,103 total

includes taxes & fees

Dec 15 - Dec 16

A well-maintained garden with a patio area, a white chair, and a small table.

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

Winchester

￥23,002 total

includes taxes & fees

Dec 15 - Dec 16

6. Calm 1 Bed Apartment with Parking, Winchester by At Hem

Winchester

Jayani

￥38,708 total

includes taxes & fees

Nov 30 - Dec 1

A dining table with a large bird-shaped vase containing yellow flowers, surrounded by wine glasses and plates.

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

Hampshire

￥38,408 total

includes taxes & fees

Nov 16 - Nov 17

A bar area with stools, a counter with various items, and a patterned floor.

8. Second Nature Southampton

Southampton City Centre

Yahong Susan

￥16,239 total

includes taxes & fees

Nov 15 - Nov 16

A balcony with wicker chairs, a table with a fruit basket and wine glasses, and a view of houses and trees.

9. Southampton Serviced Apartment

Bassett

Emma

￥37,986 total

includes taxes & fees

Nov 15 - Nov 16

A traditional pub named "The Duke of Wellington" with a white facade, timber framing, and hanging flower baskets.

10. Beddoe Apartments

Eastleigh

Alan

￥41,151 total

includes taxes & fees

Nov 15 - Nov 16

A room with a bed, a chair, a table, and a window with curtains.

11. Settle Southampton

Freemantle

Chris

￥19,274 total

includes taxes & fees

Nov 15 - Nov 16

A modern black building with a wooden fence in front.

12. Suetts Farm Barns

Southampton

￥199,249 total

includes taxes & fees

Dec 14 - Dec 15

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

13. The Shack Cabin Sleeps 3 With Enclosed Garden

Waterlooville

￥30,343 total

includes taxes & fees

Nov 22 - Nov 23

A grassy field with a wooden fence and a bush in the foreground.

14. Stone Circle Glamping

Durrington

Darnell

￥11,422 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a wooden bed, white bedding, an orange throw blanket, a white nightstand, a red vase, and abstract wall art.

15. Orchard Road

Southsea

￥9,403 total

includes taxes & fees

Nov 15 - Nov 16

A round mirror with a woven frame reflecting a dining area with a table and chairs.

16. Hamilton House

Southsea

￥21,463 total

includes taxes & fees

Nov 15 - Nov 16

17. Francis Avenue

Southsea

￥7,385 total

includes taxes & fees

Nov 15 - Nov 16

A window with a pink cushion, a vase with red flowers, and a view of houses and greenery.

18. Cleveland Road

Southsea

￥18,615 total

includes taxes & fees

Nov 15 - Nov 16

A modern bathroom with a green wall, a white sink, and a grey sofa.

19. Peartree Serviced Apartments

Salisbury

Stephanie

￥20,896 total

includes taxes & fees

Nov 15 - Nov 16

20. The South Coast Snug

Fareham

Nikki

￥11,858 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Winchester Hotel Reviews

A covered walkway with potted plants, a modern building with vertical wooden slats, and a glass entrance.

The Fox

Winchester

10/10 Excellent

Karin

A bedroom with a bed, a chair, a desk, and bookshelves.

The Black Hole

Winchester City Center

10/10 Excellent

Paul

A bedroom with a large bed, two bedside lamps, a wooden headboard, a bathtub, and a small table with a plant.

The Grosvenor Stockbridge

Stockbridge

10/10 Excellent

Faith

A car park sign for hotel residents, a vintage car, and a brick building with outdoor seating.

Wykeham Arms

Winchester City Center

10/10 Excellent

Property managed to get it just right! Super historical and atmospheric yet still very comfortable. The bed was cozy and the rooms quiet. Thoroughly enjoyed our stay and would gladly stay here again. Breakfast was made to order and excellent! Parking was tight yet present and free. Hotel was 3 blocks from city center and 2 blocks from cathedral. Perfect placement. Do yourself a favor and choose to stay here!!

Johannes

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

The White Star Tavern

Southampton City Centre

10/10 Excellent

We booked this hotel for a two night stay - pre cruise. We are still in awe of our stay here at The White Star Tavern Hotel. From the moment we walked through the door right through to when we left for our cruise 2 days later the staff, Bridgit, Emma, Becca, Mina, Jack, Mack, Kyle, everyone was just amazing, friendly, professional, fun, helpful....The Best!! The Pub restaurant is just amazing. Best hot breakfast menu along with superb food for dinner & lunch. Bartenders, Jack & Mack make the...

Nancy

A cozy room with a stone fireplace, wooden beams, and framed pictures on the wall.

The White Hart, South Harting

Petersfield

10/10 Excellent

Michael

A brick building with a large umbrella patio area, outdoor seating, and a stone wall.

The Peat Spade Inn

Stockbridge

10/10 Excellent

Quaint property with rooms in the main building and in an outer building across a patio with table seating where we had a quiet, well-equipped, modern room. The Inn is a short walk to a scenic marsh and pond with fish/eel traps and a bench for savoring the peaceful view. The town of Stockbridge, about a mile away, is wonderful for window shopping (and purchasing!) and is the start of a beautiful picturesque 'marsh walk' through grazing cows and lovely pastures. We found their restaurant had a...

EILEEN

A brick building with a sign reading "Ennios" and a chalkboard sign stating "Open for Lunch & Dinner."

Ennios Boutique Hotel Rooms

Southampton City Centre

10/10 Excellent

Scott

A large, historic building with a Tudor-style architecture, featuring multiple chimneys and a prominent tower.

Forest Park Country Hotel & Inn, Brockenhurst, New Forest

Brockenhurst

10/10 Excellent

Stacy

A serene riverside view with lush greenery and a traditional house with a blue roof.

The Old Mill

Lymington

10/10 Excellent

nicholas

A traditional room with a fireplace, multiple seating areas, and a large window.

The White Horse Hotel, Romsey, Hampshire

Romsey

10/10 Excellent

WILLIAM

A stone pathway leading through a garden with a wrought iron gate.

Four Seasons Hotel Hampshire

Hook

10/10 Excellent

Melanie

Find out more about Winchester

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Frequently Asked Questions

Can I find vacation rentals in Winchester?

Yes, we give you a choice of vacation rentals in Winchester close to Winchester Science Centre and Planetarium, or you can go with 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 vacation home rentals in Winchester?

Unique waterside home in stunning location.: This vacation 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 you can cook with friends or family.

How many vacation rentals are there in Winchester?

Expedia has 37 vacation 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 family-friendly sights, whereas cultural attractions include Great Hall and Theatre Royal Winchester. While in the area, you can also visit popular places like Southampton Cruise Terminal and New Forest National Park.

What’s a vacation rental in Winchester like?

A vacation rental is a private property where you can stay for several days or longer in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.

Winchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester vacation rentals

1. Settle Winchester

2. Winchester Wessex Hotel by Sunday Twin Room

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

4. Aethelred Annexe - New Build with Full Amenities

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

6. Calm 1 Bed Apartment with Parking, Winchester by At Hem

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

8. Second Nature Southampton

9. Southampton Serviced Apartment

10. Beddoe Apartments

11. Settle Southampton

12. Suetts Farm Barns

13. The Shack Cabin Sleeps 3 With Enclosed Garden

14. Stone Circle Glamping

15. Orchard Road

16. Hamilton House

17. Francis Avenue

18. Cleveland Road

19. Peartree Serviced Apartments

20. The South Coast Snug

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

The Fox

10/10 Excellent

Find out more about Winchester

Frequently Asked Questions

Can I find vacation rentals in Winchester?

What are some of the best vacation home rentals in Winchester?

How many vacation rentals are there in Winchester?

What’s there to see and do in Winchester?

What’s a vacation rental in Winchester like?