A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winchester vacation rentals

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

1. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is AED 152
AED 449 total
includes taxes & fees
5 Nov - 6 Nov
Settle Winchester
A modern interior with a staircase, seating area, and a green wall.

2. Winchester Wessex Hotel by Sunday Twin Room

Winchester Wessex Hotel by Sunday Twin Room
Winchester City Center
9.4 out of 10, Exceptional, (40 reviews)
"Didn’t have Kitchen like advertised, no fridge unfortunately "
United Kingdom
Hayden
The price is AED 437
AED 437 total
includes taxes & fees
8 Nov - 9 Nov
Winchester Wessex Hotel by Sunday Twin Room
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

Garden room, central Winchester – self-contained, kitchenette & parking
Winchester
The price is AED 463
AED 483 total
includes taxes & fees
8 Nov - 9 Nov
Garden room, central Winchester – self-contained, kitchenette & parking
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

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
The price is AED 537
AED 980 total
includes taxes & fees
19 Nov - 20 Nov
Winchester City Centre Flat/Sleeps 6/Free Parking
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

Aethelred Annexe - New Build with Full Amenities
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Had a lovely stay at the Aethelred Annexe! Great amenities and an incredibly generous host. It felt very warm and cozy and the bed was super comfy. Great location for a quick drive/ bus into the city centre. Would absolutely recommend."
United States
Andrea W.
The price is AED 443
AED 493 total
includes taxes & fees
5 Nov - 6 Nov
Aethelred Annexe - New Build with Full Amenities
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

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
8.6 out of 10, Excellent, (7 reviews)
"Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ."
United Kingdom
Nicola H.
The price is AED 556
AED 738 total
includes taxes & fees
5 Nov - 6 Nov
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
A modern interior with a red sofa, black chairs, and a patterned floor.

7. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,365 reviews)
"Great location and friendly staff!"
United States
Gary
The price is AED 316
AED 379 total
includes taxes & fees
13 Nov - 14 Nov
Second Nature Southampton
A kitchen counter with vegetables, a sink, and potted plants.

8. Beddoe Apartments

Beddoe Apartments
3.0 star property
Eastleigh
7.8 out of 10, Good, (20 reviews)
"Ideal for couple of nights stay. Easy parking was a bonus. "
United Kingdom
Alan
The price is AED 493
AED 813 total
includes taxes & fees
8 Nov - 9 Nov
Beddoe Apartments
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

9. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.2 out of 10, Very good, (14 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is AED 194
AED 454 total
includes taxes & fees
15 Nov - 16 Nov
Settle Southampton
A balcony with wicker chairs, a table with a fruit basket and wine glasses, and a view of houses and trees.

10. Southampton Serviced Apartment

Southampton Serviced Apartment
4.0 star property
Bassett
8.6 out of 10, Excellent, (188 reviews)
"Clean rooms, spacious enough for two for a weekend/long weekend. Easy access to Southampton City centre on the No1 bus, which runs right past the front door. Plenty of parking front and rear to service all the apartments."
United Kingdom
Emma
The price is AED 739
AED 887 total
includes taxes & fees
8 Nov - 9 Nov
Southampton Serviced Apartment
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

The Shack Cabin Sleeps 3 With Enclosed Garden
2.0 star property
Waterlooville
The price is AED 590
AED 708 total
includes taxes & fees
19 Nov - 20 Nov
The Shack Cabin Sleeps 3 With Enclosed Garden
A tent with a bed inside, a colorful rug, and a sign on the ground.

12. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.6 out of 10, Excellent, (21 reviews)
"Cozy place to stay, it is near a road but it didn’t bother me. It is as advertised"
Canada
Darnell
The price is AED 222
AED 266 total
includes taxes & fees
5 Nov - 6 Nov
Stone Circle Glamping
A dining area with a view of a swimming pool, a table with food, and a chair.

13. Beam Cottage

Beam Cottage
3.0 star property
Southampton
The price is AED 9,723
AED 11,668 total
includes taxes & fees
17 Nov - 18 Nov
Beam Cottage
A dining table set with plates, cutlery, and a glass vase with yellow flowers.

14. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
The price is AED 493
AED 745 total
includes taxes & fees
29 Nov - 30 Nov
3 Bedrooms house ideal for long Stays!
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

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is AED 419
AED 650 total
includes taxes & fees
5 Nov - 6 Nov
The Riley Stable- Cozy Getaway
A wooden cabin with an open door, surrounded by lush greenery.

16. Wigwam Holidays Cabin With Ensuite without Pergola

Wigwam Holidays Cabin With Ensuite without Pergola
Chawton
10.0 out of 10, Exceptional, (9 reviews)
"The cabin has everything you need for a short stay, it's a great place for children and would easily for a family of three. Lovely surroundings for someone who loves nature and walks."
United States
NASTASSIA N.
The price is AED 542
AED 542 total
includes taxes & fees
5 Nov - 6 Nov
Wigwam Holidays Cabin With Ensuite without Pergola
A bedroom with a bed, a chair, a TV, and a window.

17. Orchard Road

Orchard Road
2.0 star property
Southsea
The price is AED 183
AED 219 total
includes taxes & fees
7 Nov - 8 Nov
Orchard Road
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.

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"This cottage was absolutely charming and exactly what our family needed for a safe comfortable place to stay."
United States
Grace O.
Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
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

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (10 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
The price is AED 399
AED 479 total
includes taxes & fees
16 Nov - 17 Nov
Charles Hope Salisbury Centre
Exterior

20. The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
7.4 out of 10, Good, (6 reviews)
"Fantastic place great location everything close by"
United Kingdom
Nikki
The price is AED 233
AED 280 total
includes taxes & fees
9 Nov - 10 Nov
The South Coast Snug
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

The Winchester Hotel & Spa

The Winchester Hotel & Spa

10/10 Excellent
"spa facilities"
Bisserka 1-night trip
Posted 11 hours ago
The Winchester Hotel & Spa

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.