Photo by Philip Halling

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Check prices for these dates

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Winson holiday 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
8.6 out of 10, Excellent, (33)
"A very peaceful stay "
United Kingdom
Fiona
The price is ฿8,203
฿9,844 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Lakes By YOO
Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher
The Clealings

Cottage in Witney

The Clealings
3.5 star property
10.0 out of 10, Exceptional, (1)
"The perfect stay for a holiday in the Cotwolds with friends and family. The owners are very nice and the property has everything we needed and more"
United Kingdom
Alessandro
The price is ฿56,398
฿56,398 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Clealings
Exterior
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 ฿3,613
฿4,335 total
includes taxes & fees
4 Jan - 5 Jan 2026
George 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, (200)
"Excellent suites and great location!"
United Kingdom
Barrie
The price is ฿2,932
฿3,519 total
includes taxes & fees
4 Jan - 5 Jan 2026
Strozzi Palace Suites by Mansley
Apartment, Ensuite (Coach House) | 1 bedroom
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 ฿2,618
฿3,142 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Coach House and The Stable
Apartment | Private kitchen | Fridge, microwave, oven, stovetop
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 ฿2,762
฿4,068 total
includes taxes & fees
2 Jan - 3 Jan 2026
Gloucester - Apartment - Sleeps 2 - Parking - 97ws
Private kitchen
Beautiful One BR Cottage in Cerney Wick

Holiday Home in Cirencester

Beautiful One BR Cottage in Cerney Wick
2.0 star property
Beautiful One BR Cottage in Cerney Wick
Deluxe Double Room, 1 Bedroom, Non Smoking | In-room safe, individually decorated, individually furnished, desk
Crescent Place by Mansley

Aparthotel in Cheltenham

Crescent Place by Mansley
3.0 star property
9.4 out of 10, Exceptional, (89)
"Good location, clean and nice rooms. "
United Kingdom
Jessica
The price is ฿2,641
฿3,169 total
includes taxes & fees
4 Jan - 5 Jan 2026
Crescent Place by Mansley
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 ฿2,758
฿3,309 total
includes taxes & fees
11 Jan - 12 Jan 2026
Old Fleece Apartments
Cottage | Interior
Dolphin House

Holiday Home in Burford

Dolphin House
3.5 star property
10.0 out of 10, Exceptional, (1)
"Perfect cottage for our family of 6. Great location with variety of dining and shopping options, perfect amount of space for the family to spread out or all be in one room together. Beautiful garden. The parking is tight for large vehicles but we made it work. The cottage is cute with historic charm and some low ceilings, but we’re all over 6’ tall found the charm worth ducking our heads for. Highly recommend the Dolphin House!"
United States
Benjamin
The price is ฿46,429
฿55,715 total
includes taxes & fees
5 Jan - 6 Jan 2026
Dolphin House
Exterior
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
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

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

10/10 Excellent
"Execellent place to go relax and take in the beautiful Cotwolds. This hotel is just perfect for a weekend break or longer. The rooms are modern, clean with all amenities you would expect from a top hotel. Breafast was amazing and the amazing staff prepared eggs for breakfast as we like. Its located so close to great day vists and if nothingbelse just in the hotel and enjoy the pool and spa and relax at the bar. We'll definitely be back soon..a great big.thank you everyone at the hotel for making our stay PERFECT ! "
Hardip 2-night trip
Posted 2 days ago
Cheltenham Chase 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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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 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.