A stone house with a sloped roof, two skylights, and a green door.

Winson Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winson holiday rentals

Reception

Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (235 reviews)
"Great location and had air con"
United Kingdom
Joanne
The price is S$122
includes taxes & fees
16 Aug - 17 Aug
Strozzi Palace Suites by Mansley
Laptop workspace, free WiFi, bed sheets

George Apartments

George Apartments
2.0 star property
Broadway
9.2 out of 10, Wonderful, (33 reviews)
"Absolutely immaculate apt. Had a double bed and then a small kitchen and bathroom that were each separated by a door. The AC was amazing. It was just right from 2 people. Check in was easy, as it was code entry. Perfect location right behind the Main Street, quite quiet. Had a little courtyard with one small bench."
Canada
Sonja
The price is S$221
includes taxes & fees
19 Jul - 20 Jul
George Apartments
Exterior

Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (120 reviews)
"Great rooms right in town centre with lovely Korean restaurant next door. Superb air con in hot weather too!"
United Kingdom
Donald
The price is S$114
includes taxes & fees
16 Aug - 17 Aug
Crescent Place by Mansley
In-room safe, iron/ironing board (on request), free WiFi

Cotswold Townhouse - Adults Only

Cotswold Townhouse - Adults Only
2.0 star property
Stow-on-the-Wold
Cotswold Townhouse - Adults Only
Front of property

Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (148 reviews)
"Great location. Beautifully kept apartment and a parking space."
United Kingdom
Titisha
The price is S$224
includes taxes & fees
16 Aug - 17 Aug
Portland Apartments
Hypo-allergenic bedding, iron/ironing board, free WiFi, bed sheets

The Lakes By YOO

The Lakes By YOO
2.5 star property
Lechlade
8.6 out of 10, Excellent, (41 reviews)
"Great stay. Thank you to Joy for her help and making such a great overnight stay for my fiancés 30th bday. Photos did not do the property justice it was so spacious including the ground floor balcony. We will be coming back and can’t wait. The food was great and so was the breakfast & pancakes!! The suites need more photos of the outside and the whole property could do with more signage it’s easy to get lost there are some signs but they’re not clear so we got lost a few times. If you’re...
United Kingdom
Josh
The price is S$414
includes taxes & fees
16 Aug - 17 Aug
The Lakes By YOO
Dishwasher, cookware/dishes/utensils

Flat 6

Flat 6
2.0 star property
Tetbury
The price is S$807
includes taxes & fees
21 Jul - 22 Jul
Flat 6
Lounge

The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
8.8 out of 10, Excellent, (45 reviews)
"Great stay "
United Kingdom
Tania
The price is S$130
includes taxes & fees
26 Jul - 27 Jul
The Coach House and The Stable
50-inch Smart TV with cable channels, TV, Netflix

Suite Life Serviced Apartments

Suite Life Serviced Apartments
4.0 star property
South Swindon
8.4 out of 10, Very good, (26 reviews)
"Enjoyed our stay band would return."
United Kingdom
Mark
The price is S$384
includes taxes & fees
26 Jul - 27 Jul
Suite Life Serviced Apartments
Living area

High Life Luxury Serviced Apartments

High Life Luxury Serviced Apartments
4.0 star property
South Swindon
6.0 out of 10, (4 reviews)
"Great location & very spacious. Decent shower, comfortable bed. A few things that need improvement. "
United Kingdom
Frances
The price is S$572
includes taxes & fees
24 Jul - 25 Jul
High Life Luxury Serviced Apartments
6 bedrooms, desk, iron/ironing board, free WiFi

Modern 6 Bedroom 4 Bath House w Parking

Modern 6 Bedroom 4 Bath House w Parking
3.5 star property
South Swindon
Modern 6 Bedroom 4 Bath House w Parking
Living area

The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel
2.0 star property
Gloucester
9.0 out of 10, Wonderful, (14 reviews)
"Almost everything about this stay was excellent. I would say that some of the interior is in need of maintenance (sagging floors) and one bathroom was tight spacing. The parking was not available but we were able to get parking nearby."
United States
Ryan
The price is S$235
includes taxes & fees
19 Jul - 20 Jul
The Judges Lodgings Boutique Hotel
Interior

The Cozy Apartment

The Cozy Apartment
2.0 star property
Gloucester
7.6 out of 10, Good, (19 reviews)
"Suited our needs perfectly for our short stay to take part in Gloucester half marathon. "
United Kingdom
Matt
The price is S$172
includes taxes & fees
19 Jul - 20 Jul
The Cozy Apartment
Exterior

Old Fleece Apartments

Old Fleece Apartments
3.5 star property
Stroud
8.6 out of 10, Excellent, (40 reviews)
"Clean room comfy bed great staff "
United Kingdom
Alan
The price is S$137
includes taxes & fees
26 Jul - 27 Jul
Old Fleece Apartments
Terrace/patio

Jasmine Cottage-2BD in Heart of Bourton

Jasmine Cottage-2BD in Heart of Bourton
3.0 star property
Cheltenham
10.0 out of 10, Exceptional, (3 reviews)
"Very thoughtfully prepared cozy space. We enjoyed staying there with our two daughters. The o communication was excellent and check in and out very seamless. Location is superb if desiring to stay in Burton in the water. Beautiful, quaint town. Only complaint was lack of cooling. Luckily able to cool off at night with windows open. We really enjoyed our stay. "
United States
Ryan
The price is S$638
includes taxes & fees
4 Aug - 5 Aug
Jasmine Cottage-2BD in Heart of Bourton
Room amenity

Spa Court

Spa Court
3.0 star property
Cheltenham
7.2 out of 10, Good, (46 reviews)
"In the centre of town .Ideal for the racecourse.Easy access,pleasant and helpful staff "
United Kingdom
Paul
The price is S$125
includes taxes & fees
20 Jul - 21 Jul
Spa Court
Fridge, dishwasher, electric kettle, toaster

Cotswold View

Cotswold View
3.0 star property
Witney
The price is S$1,063
includes taxes & fees
23 Jul - 24 Jul
Cotswold View
Exterior

Greystones Cottage

Greystones Cottage
3.5 star property
Cheltenham
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic stay, would recommend."
United Kingdom
Caroline
Greystones Cottage
Private kitchen

Nelson Serviced Apartments

Nelson Serviced Apartments
3.5 star property
Gloucester
6.6 out of 10, (34 reviews)
"Great apartment at Friary but our room was on 3rd floor with no elevator which could be a struggle for some. "
United States
Tim
The price is S$196
includes taxes & fees
16 Aug - 17 Aug
Nelson Serviced Apartments
Exterior

Windsor Cottage-Bolthole in heart of CN

Windsor Cottage-Bolthole in heart of CN
3.0 star property
Chipping Norton
10.0 out of 10, Exceptional, (3 reviews)
"We loved our stay in Chipping Norton, the place was perfect size for our party of 3, great location, and ridiculously cute :) only wished we could have stayed longer."
Canada
Diane
The price is S$432
includes taxes & fees
23 Jul - 24 Jul
Windsor Cottage-Bolthole in heart of CN
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winson Hotel Reviews

Queens Hotel Cheltenham

Queens Hotel Cheltenham

10/10 Excellent
"Very helpfull staff, outside terrace dining was very good and the food at dinner and breakfast was very good as well. One nice youch was the provision of fresh milk in the minibar. Parking seemed expensive but the norm for Cheltenham."
David 1-night trip
Posted 8 hours ago
Queens Hotel Cheltenham

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’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.