Winchester Vacation Rentals

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Aug 30 - Aug 31
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Aug 31 - Sep 1
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Sep 5 - Sep 7
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Sep 12 - Sep 14

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
2 bedrooms, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (1)
"Lovely place to stay, friendly host who is very helpful with ideas. Cabin was homely and cosy, kids loved the bed set up. Outdoor kitchen was perfect, we cooked burgers and steaks to perfection. Kids where given the run of the garden and the boys have told me to give a 5 star review. Thank you for having us."
The price is CA $256
CA $347 total
includes taxes & fees
Sep 8 - Sep 9
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
room2 Southampton Hometel
Front of property

room2 Southampton Hometel

4.0 star property
9.4 out of 10, Exceptional, (1073)
" Staff very helpful and location is very good."
The price is CA $148
CA $178 total
includes taxes & fees
Sep 4 - Sep 5
room2 Southampton Hometel
Southampton Serviced Apartment
Balcony view

Southampton Serviced Apartment

4.0 star property
8.4 out of 10, Very good, (171)
"It was in a good location. The communication was perfect. "
Southampton Serviced Apartment
The Walls
Lobby sitting area

The Walls

2.0 star property
4.6 out of 10, (7)
"It was ok for a quick stay. nothing fancy. "
The Walls
Peartree Serviced Apartments
Studio, 1 Queen Bed | Private kitchen

Peartree Serviced Apartments

3.5 star property
9.6 out of 10, Exceptional, (284)
"We‘ve only been there for one night. In our opinion the apartment was very clean and tidy. The biggest issue was that our apartment (family apartment) had no windows in the bedrooms, so there was no possibility to get really fresh air in there. We were really happy about the little breakfast gifts they had there. "
The price is CA $180
CA $217 total
includes taxes & fees
Sep 7 - Sep 8
Peartree Serviced Apartments
The Madison
Superior Studio

The Madison

3.0 star property
9.4 out of 10, Exceptional, (26)
"Stunning property, host was lovely very accomodating quick to respond, would definitely use again, we were working from early hours to late eveming so didn't have chance to shop or eat oit on thia occasion but judging by everything else this host and property offered i would give 10 out of 10 on all "
The Madison
Bayview Apartments
Shared kitchen

Bayview Apartments

2.0 star property
7.0 out of 10, Good, (2)
"To be honest although the apartment was really nice we didn’t have hardly any knives and forks and spoons for 5 people, the fridge was filthy and the cooking equipment was old worn out and filthy. For nearly £300 for one night we expected better "
The price is CA $247
CA $297 total
includes taxes & fees
Sep 8 - Sep 9
Bayview Apartments
Gunwharf Quays Apartments
Front of property

Gunwharf Quays Apartments

3.5 star property
8.2 out of 10, Very good, (59)
"Excellent apartment. Great location, great size, clean and good facilities. Great stay, will definitely stay again"
Gunwharf Quays Apartments
Pinnacle Suites
Deluxe Room, 1 Double Bed, Harbour View

Pinnacle Suites

3.0 star property
9.8 out of 10, Exceptional, (22)
"If I could rate it higher I would. Super friendly, great location, very comfortable rooms (even with AC, a big plus!)"
The price is CA $234
CA $281 total
includes taxes & fees
Sep 6 - Sep 7
Pinnacle Suites
Charming 2-bed Apartment in Central Southampton
Apartment | Private kitchen

Charming 2-bed Apartment in Central Southampton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
The price is CA $404
CA $485 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bed Apartment in Central Southampton
Superyacht on 5* Ocean Village Marina, Southampton
Marina

Superyacht on 5* Ocean Village Marina, Southampton

9.6 out of 10, Exceptional, (7)
"The yacht Ohana is a great place to stay with excellent facilities and in a fab location close to bars and restaurants.A very helpful owner made our weekend perfect! "
The price is CA $399
CA $535 total
includes taxes & fees
Sep 3 - Sep 4
Superyacht on 5* Ocean Village Marina, Southampton
Central Versatile Studio
Studio | Living area

Central Versatile Studio

2.0 star property
6.0 out of 10, (1)
"property just down rd from the hard. Hard to find without prior knowledge. Entry was difficult becuase the entry system at first took a lot of doing. It is on a safe system that needs imput from the owners and a no to get the small safe to drop and reveal the key to apt. Not able to get TV or internet until landlady came on sun morning. Phone conversation was not good at all. Frequently breaking down when asking questions. No instructions at all in apt to get started. No hot water...
The price is CA $155
CA $241 total
includes taxes & fees
Sep 1 - Sep 2
Central Versatile Studio
Beautiful 2 bedroom full-furnished semi-detached house with parking
Fridge, microwave, oven, dishwasher

Beautiful 2 bedroom full-furnished semi-detached house with parking

9.4 out of 10, Exceptional, (6)
"Everything was perfect!"
The price is CA $251
CA $286 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful 2 bedroom full-furnished semi-detached house with parking
Mill Rythe Coastal Village
Children's play area - outdoor

Mill Rythe Coastal Village

2.0 star property
9.2 out of 10, Wonderful, (43)
"We loved our stay, great for families! "
Mill Rythe Coastal Village
Central 3BR Home with Hot Tub Sleeps 10
Family House, Garden View | Terrace/patio

Central 3BR Home with Hot Tub Sleeps 10

2.0 star property
4.0 out of 10, (1)
"Considering the price, we had high hopes for our stay at this house, but unfortunately, we were quite disappointed. Upon arrival, we found the property was not very clean. There was urine left in the upstairs toilet, the downstairs bathroom was dusty with hair around the toilet, and the bath mat had been folded up while still wet. We also noticed a live worm or parasite on the window sill, which was very off-putting. The towels provided, which were left in a pile in the middle room, had an...
The price is CA $201
CA $315 total
includes taxes & fees
Sep 30 - Oct 1
Central 3BR Home with Hot Tub Sleeps 10
Stunning Compact Studio in Portsea
Studio | Private kitchen

Stunning Compact Studio in Portsea

2.0 star property
2.0 out of 10, (1)
"No ventilation, the apartment has no WINDOWS, accept for 2 roof lights which were too high to reach. The property was booked for 3 people, I rang and confirmed but regardless there was no linen or pillows for the 3rd person."
The price is CA $100
CA $176 total
includes taxes & fees
Sep 17 - Sep 18
Stunning Compact Studio in Portsea
City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium
Fridge, microwave, oven, coffee/tea maker

City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium

The price is CA $1,420
CA $1,605 total
includes taxes & fees
Aug 31 - Sep 1
City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium
Cosy 3 Bed Flat in Southsea
House, City View | Living area

Cosy 3 Bed Flat in Southsea

2.0 star property
6.0 out of 10, (1)
"There was no light on the Holloway. No parking until 7pm. Entrance was not very welcoming. Though house was spacious. "
The price is CA $167
CA $275 total
includes taxes & fees
Sep 1 - Sep 2
Cosy 3 Bed Flat in Southsea
Catherine House
Front of property

Catherine House

2.0 star property
5.6 out of 10, (7)
"Good city centre location, easy access to Portsmouth City and close to public transport options for other places. Unique style of accommodation with "flats" each having 4 ensuite bedrooms and shared kitchen & lounging area."
Catherine House
40 foot luxury yacht on 5* Ocean Village Marina
Marina

40 foot luxury yacht on 5* Ocean Village Marina

10.0 out of 10, Exceptional, (2)
"We decided to try something new instead of hotel so booked the yacht. Great experience. Marina and boat were lovely. Lots of restaurants and easy to walk around and explore. Steve and Miros went over and above to make sure our stay was great and even picked us up from cruise port and drove us to airport hotel the next day. Would highly recommend . "
The price is CA $276
CA $386 total
includes taxes & fees
Sep 1 - Sep 2
40 foot luxury yacht on 5* Ocean Village Marina
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

Find out more about Winchester

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $100 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 vacation 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 vacation.

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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Purple Cloud Cottage: This vacation home rental outside Winchester is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a full-sized fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winchester?

Expedia has 34 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 Jane Austen's House. 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.