Photo by Philip Halling

Winson Holiday Rentals

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Our top choices for Winson holiday rentals

The Lakes By YOO

The Lakes By YOO
5.0 star property
Lechlade
8.6 out of 10, Excellent, (33)
"A very peaceful stay "
United Kingdom
Fiona
The price is NZ$547
includes taxes & fees
4 Jan - 5 Jan
The Lakes By YOO

Beautiful 2 Bedroom Apartment With Parking in The Docks

Beautiful 2 Bedroom Apartment With Parking in The Docks
4.0 star property
Gloucester
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

Hobbes Cottage

Hobbes Cottage
3.5 star property
Malmesbury
10.0 out of 10, Exceptional, (2)
"A lovely cottage with history and character. As mentioned in the listings it would not be suitable for someone very tall or with difficulties. Facilities are excellent everything you need supplied. Parking is free but beware spaces can be all taken - it states 23 hours stay - no return for an hour, so be aware there is a car park attendant around! Cottage is within easy reach of the town and Abbey. A lovely stay"
United Kingdom
Pat
The price is NZ$1,124
includes taxes & fees
9 Jan - 10 Jan
Hobbes Cottage

Windsor Cottage-Bolthole in heart of CN

Windsor Cottage-Bolthole in heart of CN
2.5 star property
Chipping Norton
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 traveller
The price is NZ$478
includes taxes & fees
13 Jan - 14 Jan
Windsor Cottage-Bolthole in heart of CN

Elliot Oliver - Modern 2 Bedroom Town Centre Apartment

Elliot Oliver - Modern 2 Bedroom Town Centre Apartment
4.0 star property
Cheltenham
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

The Cozy Apartment

The Cozy Apartment
2.0 star property
Gloucester
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

The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
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 NZ$174
includes taxes & fees
18 Jan - 19 Jan
The Coach House and The Stable

George Apartments

George Apartments
2.0 star property
Broadway
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 NZ$241
includes taxes & fees
4 Jan - 5 Jan
George Apartments

Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
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 NZ$299
includes taxes & fees
25 Jan - 26 Jan
Portland Apartments

Old Fleece Apartments

Old Fleece Apartments
3.5 star property
Stroud
8.6 out of 10, Excellent, (39)
"Far better than expected for the price will use again"
United Kingdom
brian
The price is NZ$184
includes taxes & fees
11 Jan - 12 Jan
Old Fleece Apartments

Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (91)
"Good location, clean and nice rooms. "
United Kingdom
Jessica
The price is NZ$176
includes taxes & fees
11 Jan - 12 Jan
Crescent Place by Mansley

2 Bed House - Sleeps 6 - Garden, Pets, Parking

2 Bed House - Sleeps 6 - Garden, Pets, Parking
3.5 star property
Cheltenham
8.0 out of 10, Very good, (1)
"Great location, cottage was cosy and spacious with good amenities. Dog friendly and we had an enjoyable stay. Good restaurants in the area too "
United Kingdom
Tina
The price is NZ$625
includes taxes & fees
25 Jan - 26 Jan
2 Bed House - Sleeps 6 - Garden, Pets, Parking

Beautiful Cotswold View

Beautiful Cotswold View
3.5 star property
Cheltenham
8.0 out of 10, Very good, (1)
"Lovely property just a short walk into the centre of Bourton on the water, though beware there is a very steep hill to climb when walking back. Very spacious. Lounge and open plan kitchen could do with a bit of an update. Fabulous views across the country side and so many different species of birds to view from the very large window in the lounge. Owners very kindly left binoculars and a bird book. Extremely quiet setting. Stayed Friday to Monday and it was a really lovely break. "
United Kingdom
Jureen
The price is NZ$1,589
includes taxes & fees
4 Jan - 5 Jan
Beautiful Cotswold View

Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (201)
"Absolutely brilliant"
United Kingdom
Philip
The price is NZ$159
includes taxes & fees
18 Jan - 19 Jan
Strozzi Palace Suites by Mansley

Eilmers Cottage Lovely 4BD in Malmesbury

Eilmers Cottage Lovely 4BD in Malmesbury
2.0 star property
Malmesbury
The price is NZ$949
includes taxes & fees
2 Jan - 3 Jan
Eilmers Cottage Lovely 4BD in Malmesbury

Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
3.5 star property
Gloucester
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 NZ$241
includes taxes & fees
11 Jan - 12 Jan
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

Magnolia Cottage

Magnolia Cottage
3.0 star property
Moreton-in-Marsh
9.8 out of 10, Exceptional, (10)
"Beautiful, spacious, well equipped and convenient quiet location near high street and train station. "
United Kingdom
STEFAN
The price is NZ$802
includes taxes & fees
22 Jan - 23 Jan
Magnolia Cottage

Cosy 2BD Cottage Near Daylesford

Cosy 2BD Cottage Near Daylesford
2.0 star property
Chipping Norton
The price is NZ$734
includes taxes & fees
2 Jan - 3 Jan
Cosy 2BD Cottage Near Daylesford

Modern 6 Bedroom 4 Bath House w Parking

Modern 6 Bedroom 4 Bath House w Parking
3.5 star property
Swindon
The price is NZ$531
includes taxes & fees
2 Jan - 3 Jan
Modern 6 Bedroom 4 Bath House w Parking

The Belmont Old Town

The Belmont Old Town
3.0 star property
Swindon
The price is NZ$290
includes taxes & fees
2 Jan - 3 Jan
The Belmont Old Town
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

Find out more about Winson

Everything you need to know about Winson 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 Winson holiday rental for you. At Expedia, you can take your pick from private holiday 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 Winson holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winson holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winson. 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 Winson 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 Winson holiday rentals we have selected for you start as low as NZ$159 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winson rentals

At Expedia, we put the best Winson 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 Winson 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 Winson 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 Winson. 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 a holiday rental in Winson?

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

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

Cheltenham Country Retreats: This holiday home rental outside of Winson offers a patio, a garden and a BBQ 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 wider area.

What’s a holiday rental in Winson like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winson. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.