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

Winson Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winson holiday rentals

A modern interior with a wooden deck overlooking a pool and water.

1. The Lakes By YOO

The Lakes By YOO
5.0 star property
Lechlade
8.6 out of 10, Excellent, (49 reviews)
"We really enjoyed our brief stay.Such charming staff. My only question would be,please keep fresh milk in the room fridge,for tea in the morning. We would like to come back to stay in one of the thank4 bed lodges,overlooking the lake,next time."
United Kingdom
Gillian
The price is S$284
includes taxes & fees
16 Nov - 17 Nov
The Lakes By YOO
A stone house with a wooden gate, a stone wall, and a garden with autumn foliage.

2. Meadow View Cottage

Meadow View Cottage
3.0 star property
Cheltenham
The price is S$1,335
includes taxes & fees
24 Oct - 25 Oct
Meadow View Cottage
A stone building with multiple windows, a garden with neatly trimmed hedges, and a pathway lined with flower pots.

3. Grey's Court Cottages

Grey's Court Cottages
3.0 star property
Southrop
8.0 out of 10, Very good, (1 review)
The price is S$616
includes taxes & fees
22 Oct - 23 Oct
Grey's Court Cottages
A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

4. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (250 reviews)
"Very nice hotel. Great stay."
United States
Thomas
The price is S$139
includes taxes & fees
1 Nov - 2 Nov
Strozzi Palace Suites by Mansley
A patio with wicker furniture, a stone wall, and a glass door leading to a room with a dining area.

5. Beautiful Cottage in Cirencester Centre

Beautiful Cottage in Cirencester Centre
2.0 star property
Cirencester
The price is S$584
includes taxes & fees
18 Oct - 19 Oct
Beautiful Cottage in Cirencester Centre
A building with a black door, a staircase leading to an upper floor, and a signboard for 'crescent place' with a website address.

6. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (151 reviews)
"Lovely, very clean and great location"
United Kingdom
Nina
The price is S$132
includes taxes & fees
18 Oct - 19 Oct
Crescent Place by Mansley
A living room with a stone wall, two armchairs, a wooden side table, and a kitchen in the background.

7. Beechwood Cottage Banham Cottages

Beechwood Cottage Banham Cottages
3.5 star property
Bourton-on-the-Water
10.0 out of 10, Exceptional, (1 review)
"We had the most marvelous stay. Girls weekend and we could walk to anywhere we needed to go. The property was beautiful and the hosts provided everything required for a wonderful weekend. Will definitely visit again."
United States
Michaela
The price is S$1,027
includes taxes & fees
27 Oct - 28 Oct
Beechwood Cottage Banham Cottages
A stone building with a white door and a small porch area with a bench and chairs.

8. 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, (5 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$421
includes taxes & fees
15 Nov - 16 Nov
Jasmine Cottage-2BD in Heart of Bourton
A room with a fireplace, a television, a dining table with chairs, a sofa, and a large window with a view of greenery.

9. 21 Montpellier Terrace

21 Montpellier Terrace
3.0 star property
The Suffolks
9.6 out of 10, Exceptional, (8 reviews)
"Amazing place right at the heart of centre. Great how who communicate well. Effortless Stay."
United Kingdom
Tarun
The price is S$196
includes taxes & fees
19 Oct - 20 Oct
21 Montpellier Terrace
A dining area with a table set for four, chairs, and a vase of flowers.

10. The Stables Banham Cottages

The Stables Banham Cottages
3.5 star property
Bourton-on-the-Water
The price is S$1,088
includes taxes & fees
21 Oct - 22 Oct
The Stables Banham Cottages
A beige building with a black door, a small set of steps, and two potted plants.

11. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (156 reviews)
"Fantastic accommodation."
United Kingdom
Helen
The price is S$204
includes taxes & fees
26 Oct - 27 Oct
Portland Apartments
A stone cottage with a thatched roof, a small garden, and a wooden bench.

12. Mayfly Cottage

Mayfly Cottage
3.5 star property
Cirencester
10.0 out of 10, Exceptional, (3 reviews)
"A lovely cosy cottage set in a beautiful area. We were made to feel very welcome. "
Australia
Ashril
The price is S$889
includes taxes & fees
31 Oct - 1 Nov
Mayfly Cottage
A traditional stone building with a sign for 'The Cotswold Perfumery' indicating it is a shop.

13. Bluebirds Cottage Light Airy 2BD Bourton

Bluebirds Cottage Light Airy 2BD Bourton
3.0 star property
Cheltenham
8.0 out of 10, Very good, (3 reviews)
"Brilliant country side stay in a lovely Cotswolds Hamlet "
United Kingdom
Adam
The price is S$466
includes taxes & fees
1 Nov - 2 Nov
Bluebirds Cottage Light Airy 2BD Bourton
A bedroom with a bed, bedside tables, a chair, a window, and a radiator.

14. George Apartments

George Apartments
2.0 star property
Broadway
9.4 out of 10, Exceptional, (56 reviews)
"Excellent location and well stocked kitchen."
United States
Elisa
The price is S$155
includes taxes & fees
25 Oct - 26 Oct
George Apartments
A neatly made bed with a tray of croissants and juice, a bottle of champagne, and two glasses of orange juice.

15. Elliot Oliver - Exquisite 2 Bedroom Apartment With Garden, Parking & EV Charger

Elliot Oliver - Exquisite 2 Bedroom Apartment With Garden, Parking & EV Charger
4.0 star property
Cheltenham
10.0 out of 10, Exceptional, (13 reviews)
"An incredible stay here! Clean friendly and very easy walking distance to everything you need"
United Kingdom
Sophie
The price is S$345
includes taxes & fees
7 Nov - 8 Nov
Elliot Oliver - Exquisite 2 Bedroom Apartment With Garden, Parking & EV Charger
A dining table with a bowl and two wine glasses, a fork, and a spoon.

16. Spa Court

Spa Court
3.0 star property
Cheltenham
7.2 out of 10, Good, (49 reviews)
"In the centre of town .Ideal for the racecourse.Easy access,pleasant and helpful staff "
United Kingdom
Paul
The price is S$124
includes taxes & fees
22 Oct - 23 Oct
Spa Court
A large stone building with multiple windows and a prominent tower.

17. Old Fleece Apartments

Old Fleece Apartments
3.5 star property
Stroud
8.8 out of 10, Excellent, (44 reviews)
"Was fab . Breakfast was delicious ."
United Kingdom
Charlotte
The price is S$134
includes taxes & fees
18 Oct - 19 Oct
Old Fleece Apartments
A tray with a scone, butter, jam, and a green teapot on a wooden table.

18. Cotswold Townhouse - Adults Only

Cotswold Townhouse - Adults Only
2.5 star property
Stow-on-the-Wold
The price is S$339
includes taxes & fees
18 Oct - 19 Oct
Cotswold Townhouse - Adults Only
A balcony with a table and chairs, a view of the cityscape, and a door leading to an interior space.

19. Elliot Oliver - Luxury 3 Bedroom Town Centre Apartment With Parking

Elliot Oliver - Luxury 3 Bedroom Town Centre Apartment With Parking
4.0 star property
Cheltenham
9.8 out of 10, Exceptional, (17 reviews)
"Great apartment, spacious and very clean. Close to shops, restaurants and pubs "
United Kingdom
Nikki
The price is S$498
includes taxes & fees
30 Oct - 31 Oct
Elliot Oliver - Luxury 3 Bedroom Town Centre Apartment With Parking
A narrow alleyway with brick buildings, a covered walkway, and small planters along the path.

20. Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment

Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment
4.0 star property
Cheltenham
9.2 out of 10, Wonderful, (27 reviews)
"Lovely apartment in the centre of Cheltenham. Very clean. Check in and out was very easy. Great communication with the owners. Highly recommend."
United Kingdom
Christopher
The price is S$383
includes taxes & fees
31 Oct - 1 Nov
Elliot Oliver - Stylish 2 Bedroom Town Centre 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

Hotel Indigo Gloucester The Forum By IHG

Hotel Indigo Gloucester The Forum By IHG

10/10 Excellent
"The location is perfect - near the train and bus station, and walking distance from all the shoos, restaurants, and sites if interest. The staff are all fabulous. The rooftop bar was lovely. My room was fantastic!"
Lisa 4-night trip
Posted 5 hours ago
Hotel Indigo Gloucester The Forum By IHG

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 Cotswold Country Park and Beach. 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.