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Winson Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Winson vacation rentals

Cabin | Hypo-allergenic bedding, iron/ironing board, free WiFi, bed sheets
The Lakes By YOO

Aparthotel in Lechlade

The Lakes By YOO
5.0 star property
8.8 out of 10, Excellent, (32)
"A very peaceful stay "
United Kingdom
Fiona
The price is ￥41,315
￥49,579 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Lakes By YOO
Studio, Ensuite (Stable) | Lounge
The Coach House and The Stable

Apartment in Stroud

The Coach House and The Stable
3.5 star property
9.0 out of 10, Wonderful, (41)
"Really lovely accommodation. Staff were very friendly and helpful and made sure check in and out was easy. We went to the pub for food and it was excellent - great menu and well cooked and presented. Staff were really helpful again Lovely area for a walk or trip to the vineyard "
United Kingdom
Helen
The price is ￥13,186
￥15,823 total
includes taxes & fees
Jan 18 - Jan 19, 2026
The Coach House and The Stable
Front of property
Portland Apartments

Aparthotel in Cheltenham

Portland Apartments
3.5 star property
9.8 out of 10, Exceptional, (137)
"•Great Location •Apartment immaculate •Tastefully decorated •Friendly hosts •A luxurious home from home •Highly recommend •Complimentary Tea, Coffee, Milk, Orange Juice and Croissants "
United Kingdom
Debra
The price is ￥22,483
￥26,979 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Portland Apartments
Reception
Strozzi Palace Suites by Mansley

Apartment in Cheltenham

Strozzi Palace Suites by Mansley
4.0 star property
9.4 out of 10, Exceptional, (199)
"Excellent suites and great location!"
United Kingdom
Barrie
The price is ￥14,540
￥17,448 total
includes taxes & fees
Dec 28 - Dec 29
Strozzi Palace Suites by Mansley
Interior
The Cozy Apartment

Aparthotel in Gloucester

The Cozy Apartment
2.0 star property
7.6 out of 10, Good, (19)
"Suited our needs perfectly for our short stay to take part in Gloucester half marathon. "
United Kingdom
Matt
The Cozy Apartment
Apartment, Private Bathroom | Exterior
Old Fleece Apartments

Apartment in Stroud

Old Fleece Apartments
3.5 star property
8.6 out of 10, Excellent, (39)
"Far better than expected for the price will use again"
United Kingdom
brian
The price is ￥13,889
￥16,667 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Old Fleece Apartments
Classic Double Room, Non Smoking | Laptop workspace, free WiFi, bed sheets
George Apartments

Aparthotel in Broadway

George Apartments
2.0 star property
9.6 out of 10, Exceptional, (18)
"The apartment was immaculate and really well appointed. It has everything you need for a short stay including coat hooks, which are so often missing in a hotel room! The apartment was ideally situated for the town with free parking. It has a noisy aircon/heating system which I tried and failed to turn off-otherwise perfect! "
United Kingdom
Lesley
The price is ￥17,287
￥20,744 total
includes taxes & fees
Jan 11 - Jan 12, 2026
George Apartments
Exterior
Crescent Place by Mansley

Aparthotel in Cheltenham

Crescent Place by Mansley
3.0 star property
9.4 out of 10, Exceptional, (88)
"Good location, clean and nice rooms. "
United Kingdom
Jessica
The price is ￥13,300
￥15,960 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Crescent Place by Mansley
Apartment | 1 bedroom, free WiFi, bed sheets
Gloucester - Apartment - Sleeps 2 - Parking - 97ws

Apartment in Gloucester

Gloucester - Apartment - Sleeps 2 - Parking - 97ws
3.0 star property
10.0 out of 10, Exceptional, (1)
"excellent location. Parking free from 3pm - 9am right outside the door. Very nicely renovated, good cooking facilities. Very friendly and helpful owner. Only downside for us was the bed is next to the wall so not so easy to get in and out of as a couple when you are old like us."
United Kingdom
Dawn
The price is ￥13,910
￥20,490 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Gloucester - Apartment - Sleeps 2 - Parking - 97ws
Apartment | Living area | Smart TV, Netflix, DVD player, streaming services
Elliot Oliver - Chic 2 Bedroom Town Centre Apartment

Apartment in Cheltenham

Elliot Oliver - Chic 2 Bedroom Town Centre Apartment
3.0 star property
10.0 out of 10, Exceptional, (1)
"Really lovely apartment, the beds are so comfy and the shower is lovely!"
United Kingdom
Lauren
Elliot Oliver - Chic 2 Bedroom Town Centre Apartment
Terrace/patio
Brookbank Close

Vacation Home in Cheltenham

Brookbank Close
4.0 star property
The price is ￥40,436
￥64,346 total
includes taxes & fees
Dec 30 - Dec 31
Brookbank Close
Luxury Apartment, Private Bathroom, City View (2 Bedrooms) | Interior
Stylish Town Centre Apartments

Apartment in Stroud

Stylish Town Centre Apartments
3.5 star property
10.0 out of 10, Exceptional, (1)
"Lovely town and great atmosphere. I would definitely stay here again! The room was cozy and well kept. "
United States
Gavin
The price is ￥36,920
￥52,743 total
includes taxes & fees
Dec 29 - Dec 30
Stylish Town Centre Apartments
48-inch flat-screen TV with digital channels, TV
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

Apartment in Gloucester

Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
3.5 star property
8.2 out of 10, Very Good, (21)
"Nice, central location. Quays nearby, so plenty of choices to eat/drink as well as the city centre being right there. Apartment was spacious, clean, recently refurbished by the look of it. Bed was comfortable, plenty of space in the apartment, nice kitchen and bathroom. "
United Kingdom
Robert
The price is ￥19,283
￥23,139 total
includes taxes & fees
Dec 25 - Dec 26
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
2 bedrooms, individually decorated, individually furnished
Beautiful 2 Bedroom Apartment With Parking in The Docks

Apartment in Gloucester

Beautiful 2 Bedroom Apartment With Parking in The Docks
4.0 star property
9.6 out of 10, Exceptional, (5)
"A lovely apartment in a perfect location. "
United Kingdom
Kim
Beautiful 2 Bedroom Apartment With Parking in The Docks
Exterior
Windsor Cottage-Bolthole in heart of CN

Vacation Home in Chipping Norton

Windsor Cottage-Bolthole in heart of CN
2.5 star property
10.0 out of 10, Exceptional, (2)
"Had a lovely stay at Windsor cottage. Well presented, great amenities and the most comfortable bed in the master bedroom. Slept like a log! Ate out in local restaurants, which were lovely especially Alberto’s Italy. There are a couple of free parking areas in town 5-10 minutes away. During our stay there was a film set in place for Father Brown and a restriction at the end of the road. It didn’t take away from our stay, but was glad of the premier inn parking just a 100m away. We pulled up to...
United Kingdom
Anonymous traveler
Windsor Cottage-Bolthole in heart of CN
Grand Apartment, 2 Bedrooms, Courtyard View | Living area | 42-inch flat-screen TV with digital channels
The Judges Lodgings Boutique Hotel

Aparthotel in Gloucester

The Judges Lodgings Boutique Hotel
2.0 star property
8.4 out of 10, Very Good, (7)
"The location was great and the area quiet. Convenient to train and bus, grocery, and local interests. Property was ok in cleanliness (white grout and subway tile require a LOT of maintenance) and the modern updates were poorly installed. Far too many bric-a-brac to keep dusted. Comfortable and spacious. "
United States
Erin
The price is ￥15,111
￥30,813 total
includes taxes & fees
Dec 26 - Dec 27
The Judges Lodgings Boutique Hotel
House, City View | 2 bedrooms, iron/ironing board, free WiFi
Central 2BD with Garden and Free Parking

Vacation Home in Cheltenham

Central 2BD with Garden and Free Parking
10.0 out of 10, Exceptional, (1)
"Lots of space and very clean. lovely"
Australia
Shan
The price is ￥31,066
￥58,413 total
includes taxes & fees
Dec 26 - Dec 27
Central 2BD with Garden and Free Parking
Property entrance
Elliot Oliver - Modern 2 Bedroom Town Centre Apartment

Apartment in Cheltenham

Elliot Oliver - Modern 2 Bedroom Town Centre Apartment
4.0 star property
9.6 out of 10, Exceptional, (5)
"Modern 2 bedroom apartment very close to the town centre. Very clean and quiet with all mod cons. TV has free Netflix included, however the couch was too small to lie down on comfortably. Only other negative was a noisy manhole cover in the street which vibrated every time a car drove over it ( not the fault of the apartment obviously). "
United Kingdom
Mr D
Elliot Oliver - Modern 2 Bedroom Town Centre Apartment
House, Patio | Living area | Flat-screen TV
Charming 2BD in the Heart of Kingham

Vacation Home in Chipping Norton

Charming 2BD in the Heart of Kingham
3.0 star property
10.0 out of 10, Exceptional, (1)
Charming 2BD in the Heart of Kingham
Interior
Elliot Oliver - Exquisite 2 Bedroom Apartment With Garden, Parking & EV Charger

Apartment in Cheltenham

Elliot Oliver - Exquisite 2 Bedroom Apartment With Garden, Parking & EV Charger
4.0 star property
10.0 out of 10, Exceptional, (9)
"Great apartment. Very clean and modern. Will definitely be staying there again."
United Kingdom
Ross
Elliot Oliver - Exquisite 2 Bedroom Apartment With Garden, Parking & EV Charger
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 Winson Hotel Reviews

Hatherley Manor Hotel & Spa

Hatherley Manor Hotel & Spa

10/10 Excellent
"Overall excellent value for money. Good breakfast and the staff were really friendly. Slightly odd smell in some of the downstairs corridors - a bit like damp? The facilities were really good, loved the spa and the gym. Beautiful property. Lots of parking. Slightly confusing information on Expedia when booking re spa access as it conflicts with some of the information on the website but wasn't a problem on arrival at the hotel. Overall enjoyed our stay "
Claire 1-night trip
Posted 2 days ago
Hatherley Manor Hotel & Spa

Find out more about Winson

Search for holiday rentals in Winson on Expedia! You can easily find your home rentals, villas, holiday apartments in Winson using one of the methods below:

  • View our selection of featured holiday rentals in Winson
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  • Enter your travel dates to view the best deals on holiday rentals in Winson while they last

Look no further and take a look at our great range of rental properties in Winson!

Frequently asked questions

Can I find a vacation rental in Winson?

Yes, there are vacation rentals close to the most popular sights in Winson, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Winson has to offer?

Cheltenham Country Retreats: This vacation home rental outside of Winson offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

What’s there to see and do in Winson?

While exploring the area, visit family-friendly sights like The Model Village, or get outside and enjoy nature at Cirencester Roman Amphitheatre. Arlington Row and Chedworth Roman Villa are a couple of places you'll find in the larger area.

What’s a vacation rental in Winson like?

A vacation rental is a private property where you can stay for a couple of days or more in Winson. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family getaway.