Photo by Philip Halling

Winson Vacation Rentals

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Check prices for these dates

Tonight
15 Dec - 16 Dec
Tomorrow
16 Dec - 17 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Winson holiday rentals

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

The Lakes By YOO

The Lakes By YOO
5.0 star property
Lechlade
8.8 out of 10, Excellent, (32)
"A very peaceful stay "
United Kingdom
Fiona
The price is RM1,073
RM1,287 total
includes taxes & fees
16 Dec - 17 Dec
The Lakes By YOO
Exterior
Crescent Place by Mansley

Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (88)
"Good location, clean and nice rooms. "
United Kingdom
Jessica
The price is RM359
RM431 total
includes taxes & fees
21 Dec - 22 Dec
Crescent Place by Mansley
Front of property
Portland Apartments

Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (136)
"•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 RM635
RM762 total
includes taxes & fees
16 Dec - 17 Dec
Portland Apartments
Laptop workspace, free WiFi, bed sheets
George Apartments

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 RM473
RM567 total
includes taxes & fees
4 Jan - 5 Jan 2026
George Apartments
Reception
Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (199)
"Excellent suites and great location!"
United Kingdom
Barrie
The price is RM384
RM460 total
includes taxes & fees
11 Jan - 12 Jan 2026
Strozzi Palace Suites by Mansley
48-inch flat-screen TV with digital channels, TV
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

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 RM586
RM703 total
includes taxes & fees
16 Dec - 17 Dec
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
Lounge
The Coach House and The Stable

The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
9.0 out of 10, Wonderful, (41)
"Great stay "
United Kingdom
Tania
The price is RM342
RM411 total
includes taxes & fees
21 Dec - 22 Dec
The Coach House and The Stable
Room amenity
Spa Court

Spa Court

Spa Court
3.0 star property
Cheltenham
7.4 out of 10, Good, (40)
"Very good, well equipped apartment in a central location."
Ireland
paul
Spa Court
50-inch Smart TV with cable channels, TV, Netflix
Suite Life Serviced Apartments

Suite Life Serviced Apartments

Suite Life Serviced Apartments
4.0 star property
Swindon
8.4 out of 10, Very good, (23)
"Always love my stays at these apartments! Feels so homely, easy location for my work and very spacious. Spotlessly clean every time & private parking right outside."
United Kingdom
Sophie
Suite Life Serviced Apartments
1 bedroom, individually decorated, individually furnished
Elliot Oliver- Charming 1 Bed Apartment

Elliot Oliver- Charming 1 Bed Apartment

Elliot Oliver- Charming 1 Bed Apartment
4.0 star property
Gloucester
10.0 out of 10, Exceptional, (7)
"Excellent apartment, very central and parking is a bonus. Plenty of eateries nearby and a few minutes walk into the city centre for shopping & sightseeing 😊 "
United Kingdom
Peter
Elliot Oliver- Charming 1 Bed Apartment
Pool
Blackthorn

Blackthorn

Blackthorn
3.0 star property
Witney
10.0 out of 10, Exceptional, (1)
"This stay at Blackthorn went above and beyond what I needed - some time and space for myself to write. In the comfort and peace of this hut in this location, I was able to write nearly 10,000 words, unheard of in my everyday busy life at home! The hut was perfect, the bed extremely comfortable with high-quality linens and duvet/pillows. Kitchen very well-supplied with everything I needed (and more). The bathroom was great too, shower a little on the less-powerful side, but I expected that seeing...
United Kingdom
Jessica
The price is RM1,397
RM1,677 total
includes taxes & fees
19 Dec - 20 Dec
Blackthorn
Free WiFi, bed sheets
Charles Hope Apartments Swindon

Charles Hope Apartments Swindon

Charles Hope Apartments Swindon
3.5 star property
Swindon
7.4 out of 10, Good, (14)
"Must visit place."
United Kingdom
MANIK PREET
Charles Hope Apartments Swindon
Desk, bed sheets
Vernon Place Accommodation

Vernon Place Accommodation

Vernon Place Accommodation
3.0 star property
Cheltenham
10.0 out of 10, Exceptional, (2)
" Excellent quiet location, close to the high street with lots of options for eating out.Well maintained property, nice and clean. Overall 5/5 Single traveller, business trip."
United Kingdom
Anonymous traveller
Vernon Place Accommodation
Living area
The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel
2.0 star property
Gloucester
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 RM315
RM706 total
includes taxes & fees
16 Dec - 17 Dec
The Judges Lodgings Boutique Hotel
Interior
Weir Cottage

Weir Cottage

Weir Cottage
3.5 star property
Cheltenham
The price is RM5,810
RM6,972 total
includes taxes & fees
19 Dec - 20 Dec
Weir Cottage
Exterior
Cheltenham Country Retreats

Cheltenham Country Retreats

Cheltenham Country Retreats
3.5 star property
Cheltenham
Cheltenham Country Retreats
Interior
Cotswold View

Cotswold View

Cotswold View
3.5 star property
Cheltenham
The price is RM2,596
RM3,115 total
includes taxes & fees
19 Dec - 20 Dec
Cotswold View
Interior
The Cozy 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
Exterior
Bears Court North Barn 8

Bears Court North Barn 8

Bears Court North Barn 8
3.0 star property
Cheltenham
The price is RM4,782
RM5,738 total
includes taxes & fees
19 Dec - 20 Dec
Bears Court North Barn 8
1 bedroom
Grigshot Apartment

Grigshot Apartment

Grigshot Apartment
4.0 star property
Stroud
9.6 out of 10, Exceptional, (9)
"A very unique interesting stay. Highly recommend it. "
United States
Gregory
The price is RM799
RM959 total
includes taxes & fees
16 Dec - 17 Dec
Grigshot Apartment
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

Mollie's Motel and Diner

Mollie's Motel and Diner

10/10 Excellent
"The rooms were very clean and had everything you could want and very good quality. The staff were very friendly and helpful."
Joanne Mary 2-night trip
Posted 12 hours ago
Mollie's Motel and Diner

Find out more about Winson

Search for holiday rentals in Winson on Expedia.co.uk! 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 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 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.