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

Winson Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winson vacation rentals

A stone wall with a metal gate, a stone building with a tiled roof, and a grassy lawn.

1. Recently converted self-contained apartment with garden in Cotswold village

Recently converted self-contained apartment with garden in Cotswold village
Poulton
9.0 out of 10, Wonderful, (49 reviews)
"The location was convenient as a base for exploring Cotswolds. The guesthouse was small for a family of three, but it had everything we needed. We would definitely consider booking this property if we visit this area again."
United States
Walter
The price is CA $112
CA $137 total
includes taxes & fees
Sep 27 - Sep 28
Recently converted self-contained apartment with garden in Cotswold village
A modern interior with a wooden deck overlooking a pool and water.

2. The Lakes By YOO

The Lakes By YOO
5.0 star property
Lechlade
8.6 out of 10, Excellent, (47 reviews)
"The room was beautiful in terms of showcase design but lacked niceties such as body lotion, biscuits for tea and no mirror other than the bathroom one to do make up check clothing etc The doors (in a shared hallway were very noisy - impossible to close quietly. The pool was full of kids playing ball so abandoned that idea The on site restaurant was ok The whole experience was NOT 5 star."
United Kingdom
Trevor
The price is CA $274
CA $329 total
includes taxes & fees
Sep 23 - Sep 24
The Lakes By YOO
A traditional stone cottage with a garden, a pathway, and parked cars.

3. Rosemary Cottage, cosy with a real fire just 5 minute walk from Arlington Row

Rosemary Cottage, cosy with a real fire just 5 minute walk from Arlington Row
Bibury
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic location. Beautiful countryside and centrally located among famous Cotswold sites. The host was very responsive and beds and sofas were comfortable. Would definitely recommend."
United States
Barrett S.
The price is CA $443
CA $644 total
includes taxes & fees
Sep 29 - Sep 30
Rosemary Cottage, cosy with a real fire just 5 minute walk from Arlington Row
A neatly made bed with a quilted headboard, two bedside tables with lamps, and a wardrobe to the right.

4. Lovely Cotswolds 1 bed nr town centre yet mins from river and countryside walks

Lovely Cotswolds 1 bed nr town centre yet mins from river and countryside walks
Cirencester
9.8 out of 10, Exceptional, (7 reviews)
"Good location. The apartment was as shown in the photos and descriptions."
United States
Cheri L.
Lovely Cotswolds 1 bed nr town centre yet mins from river and countryside walks
A bedroom with a bed, bedside tables, a chair, a window, and a radiator.

5. George Apartments

George Apartments
2.0 star property
Broadway
9.4 out of 10, Exceptional, (55 reviews)
"Excellent location and well stocked kitchen."
United States
Elisa
The price is CA $162
CA $194 total
includes taxes & fees
Sep 24 - Sep 25
George Apartments
A cozy room with a bed, a small table, a sofa, and a view of the outdoors.

6. The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
8.8 out of 10, Excellent, (47 reviews)
"Great stay "
United Kingdom
Tania
The price is CA $133
CA $159 total
includes taxes & fees
Oct 12 - Oct 13
The Coach House and The Stable
A stone building with multiple windows, a garden with neatly trimmed hedges, and a pathway lined with flower pots.

7. Grey's Court Cottages

Grey's Court Cottages
3.0 star property
Southrop
The price is CA $475
CA $570 total
includes taxes & fees
Oct 17 - Oct 18
Grey's Court Cottages
A building with a black door, a staircase leading to an upper floor, and a signboard for 'crescent place' with a website address.

8. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.2 out of 10, Wonderful, (140 reviews)
"Lovely, very clean and great location"
United Kingdom
Nina
The price is CA $126
CA $151 total
includes taxes & fees
Oct 18 - Oct 19
Crescent Place by Mansley
A dining table with a bowl and two wine glasses, a fork, and a spoon.

9. 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 CA $86
CA $131 total
includes taxes & fees
Oct 4 - Oct 5
Spa Court
A stone cottage with a thatched roof, a small garden, and a wooden bench.

10. 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 CA $815
CA $978 total
includes taxes & fees
Sep 30 - Oct 1
Mayfly Cottage
A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

11. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (246 reviews)
"Very nice hotel. Great stay."
United States
Thomas
The price is CA $131
CA $157 total
includes taxes & fees
Sep 27 - Sep 28
Strozzi Palace Suites by Mansley
A large stone building with multiple windows and a prominent tower.

12. Old Fleece Apartments

Old Fleece Apartments
3.5 star property
Stroud
8.6 out of 10, Excellent, (42 reviews)
"Clean room comfy bed great staff "
United Kingdom
Alan
The price is CA $124
CA $148 total
includes taxes & fees
Oct 4 - Oct 5
Old Fleece Apartments
A spacious living area with a large dining table, a sofa, and a TV mounted on the wall.

13. Period Cotswold Cottage with outdoor bar & open views

Period Cotswold Cottage with outdoor bar & open views
Milton-under-Wychwood
10.0 out of 10, Exceptional, (1 review)
"My husband, knowing how much we both love the Cotswolds, booked this cottage as a last-minute surprise, to wrap up our trip to the UK, to celebrate my birthday. What an absolute delight to spend an evening at Sunnybank Cottage. I was smitten from the moment we walked in. Beautifully appointed, wonderful location, and an absolute highlight in a busy agenda. I so wish we would have had more time to linger. I spent about 10 minutes just gazing across the picturesque landscape. It was a perfect...
United States
Brent
The price is CA $448
CA $785 total
includes taxes & fees
Oct 1 - Oct 2
Period Cotswold Cottage with outdoor bar & open views
A stone building with a window, surrounded by lush green foliage and purple wisteria vines.

14. 1 bedroom accommodation in Chedworth, near Cheltenham

1 bedroom accommodation in Chedworth, near Cheltenham
Chedworth, near Cheltenham
10.0 out of 10, Exceptional, (24 reviews)
"Very relaxed and quiet location. Cottage well appointed."
United States
Nigel Coote
The price is CA $948
CA $948 total
includes taxes & fees
Oct 18 - Oct 19
1 bedroom accommodation in Chedworth, near Cheltenham
A beige building with a black door, a small set of steps, and two potted plants.

15. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (154 reviews)
"Fantastic accommodation."
United Kingdom
Helen
The price is CA $186
CA $223 total
includes taxes & fees
Oct 12 - Oct 13
Portland Apartments
A dining area with a table set for four, chairs, and a vase of flowers.

16. The Stables Banham Cottages

The Stables Banham Cottages
3.5 star property
Bourton-on-the-Water
The price is CA $697
CA $1,034 total
includes taxes & fees
Sep 23 - Sep 24
The Stables Banham Cottages
A living room with a TV, sofa, armchair, and a fireplace.

17. Cosy Cotswold cottage a short walk from cafes, shops, pubs and restaurants

Cosy Cotswold cottage a short walk from cafes, shops, pubs and restaurants
Malmesbury
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful character property, very in keeping with the gorgeous town it’s situated in. We really enjoyed our stay and appreciated how close it is to the town, the little sunny yard, the lovely bedroom in the eaves and how comfortable the beds are. Malmsbury itself is a lovely town with local shops and eateries, and we did a long walk on the Saturday, following a route from a book at the house. Highly recommend "
United States
Tamzyn H.
The price is CA $258
CA $504 total
includes taxes & fees
Sep 23 - Sep 24
Cosy Cotswold cottage a short walk from cafes, shops, pubs and restaurants
A spacious living room with a leather sofa, a coffee table with a tray, and a wooden cabinet.

18. The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel
3.5 star property
Gloucester
9.0 out of 10, Wonderful, (18 reviews)
"The apartment was brilliant grrat bathrooms and the bed was amazingly comfortable, the kitch area was brilliant "
United Kingdom
Andrew
The price is CA $125
CA $285 total
includes taxes & fees
Oct 2 - Oct 3
The Judges Lodgings Boutique Hotel
A spacious living room with a fireplace, comfortable seating, a dining area, and large windows offering a view of the outdoors.

19. Beautiful & spacious Regency apt in centre Cheltenham, free parking

Beautiful & spacious Regency apt in centre Cheltenham, free parking
Montpellier
9.8 out of 10, Exceptional, (21 reviews)
"Lovely property, comfortable and location is great for exploring the Cotswolds."
United Kingdom
Carol W.
The price is CA $160
CA $384 total
includes taxes & fees
Sep 24 - Sep 25
Beautiful & spacious Regency apt in centre Cheltenham, free parking
A dining area with a wooden table and chairs, a vase of flowers, and a mirror on the wall.

20. The Haybarn Banham Cottages

The Haybarn Banham Cottages
3.5 star property
Bourton-on-the-Water
10.0 out of 10, Exceptional, (1 review)
"Great place to stay!"
United States
Velia
The price is CA $821
CA $1,163 total
includes taxes & fees
Oct 14 - Oct 15
The Haybarn Banham Cottages
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
"Great place... lovely rooms... nice bar and outside area. Breakfast good and use of a spa. No complaints at all."
Malcolm 1-night trip
Posted less than an hour ago
Cheltenham Chase Hotel & Spa

Find out more about Winson

Everything you need to know about Winson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winson vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winson vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winson vacation rentals we have selected for you start as low as CA $148 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 vacation 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 vacation.

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 vacation rental in Winson?

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

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

Beautiful Cotswolds farm house with period features and a beautiful garden.: This vacation home rental outside of Winson is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

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 larger area.

What’s a vacation rental in Winson like?

A vacation rental is a private property where you can stay for a couple of days or more in Winson. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family getaway.