Winson Vacation Rentals from CA $108: Short-Term Rentals for 2026

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Our top choices for Winson vacation rentals

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

1. The Lakes By YOO

Lechlade

Mathew

CA $331 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Poulton

Walter

CA $147 total

includes taxes & fees

Nov 15 - Nov 16

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

Bibury

Barrett S.

CA $496 total

includes taxes & fees

Nov 11 - Nov 12

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

Cirencester

Cheri L.

CA $252 total

includes taxes & fees

Nov 9 - Nov 10

A stone building with a window, surrounded by lush green foliage and purple wisteria vines.

5. 1 bedroom accommodation in Chedworth, near Cheltenham

Chedworth, near Cheltenham

Nigel Coote

CA $598 total

includes taxes & fees

Nov 20 - Nov 21

A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

6. Strozzi Palace Suites by Mansley

Cheltenham

Roy

CA $140 total

includes taxes & fees

Nov 22 - Nov 23

A building with a black door, a staircase leading to an upper floor, and a signboard for 'crescent place' with a website address.

7. Crescent Place by Mansley

Cheltenham

Simon

CA $130 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with multiple windows, a garden with neatly trimmed hedges, and a pathway lined with flower pots.

8. Grey's Court Cottages

Southrop

CA $677 total

includes taxes & fees

Dec 6 - Dec 7

A dining area with a wooden table and chairs, a vase of flowers, and a mirror on the wall.

9. The Haybarn Banham Cottages

Bourton-on-the-Water

Velia

CA $749 total

includes taxes & fees

Nov 8 - Nov 9

A sign for Cotswold Lavender Growers and Distillers.

10. Molly's Bit

Chipping Norton

CA $565 total

includes taxes & fees

Nov 30 - Dec 1

A living room with a stone wall, two armchairs, a wooden side table, and a kitchen in the background.

11. Beechwood Cottage Banham Cottages

Bourton-on-the-Water

Kent

CA $945 total

includes taxes & fees

Nov 15 - Nov 16

A green door with a sign above it that reads 'The Townhouse.'

Bourton-on-the-Water

CA $1,043 total

includes taxes & fees

Nov 19 - Nov 20

A rustic interior with a stone fireplace, wooden beams, a dining area, and a cozy seating arrangement.

16. Bourton on the Water Country Chic Authentic Cottage

Bourton-on-the-Water

Amy R.

A bedroom with a bed, bedside tables, a chair, a window, and a radiator.

17. George Apartments

Broadway

Peter

CA $239 total

includes taxes & fees

Dec 6 - Dec 7

A room with a fireplace, a television, a dining table with chairs, a sofa, and a large window with a view of greenery.

18. 21 Montpellier Terrace

The Suffolks

Tarun

CA $352 total

includes taxes & fees

Nov 11 - Nov 12

A large stone building with multiple windows and a prominent tower.

19. Old Fleece Apartments

Stroud

Charlotte

CA $149 total

includes taxes & fees

Nov 15 - Nov 16

A stone house with a pitched roof, a small window, and a door.

20. The Clock Tower

Cirencester

Gemma

CA $1,409 total

includes taxes & fees

Nov 11 - Nov 12

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Find vacation rentals that suit your style

Top Winson Hotel Reviews

An outdoor patio area with wicker furniture, stone walls, and string lights.

Wild Thyme & Honey

Cirencester

10/10 Excellent

My husband and I stayed here while visiting the Cotswold's and it was a fantastic stay. It is close to all the main little towns you would want to see (all within a 45min drive) but, it is also completed secluded which is so nice too. The hotel itself is lovely- warm, cozy, modern, clean. They have a beautiful outdoor terrace, opened even in the winter. The restaurant is great too, when we came it was very busy and they ran out of a lot of their menu options which was a bit annoying but, we it...

Jesse

A green door with a decorative arch, surrounded by lush greenery and flowering pots.

Stratton House Hotel & Spa

Cirencester

10/10 Excellent

paul

The Colesbourne Inn

Cheltenham

10/10 Excellent

Janaya

A cozy living room with a fireplace, plaid carpet, leather sofas, and a dining area with wooden furniture.

Thames Head Inn

Cirencester

10/10 Excellent

We loved our stay at this hotel! The rooms were quaint and well made up. There was even a bathtub in our room, which was a game changer! We also really enjoyed dining at the property's pub, and the food was amazing! Very much enjoyed the fish and chips and the lamb special they were serving. The location is perfect if you're exploring the surrounding Cotswolds towns and don't want to stay in the center of the action. We would definitely return to this hotel when we come back to the Cotswolds in...

Lindsay

A traditional stone building with multiple signs indicating it is an inn offering a bar, restaurant, and hotel services.

Inn For All Seasons

Burford

10/10 Excellent

Darrell

A stone house with a wooden porch, a small garden with pebbles, and a white picket fence.

The Feathered Nest Country Inn

Chipping Norton

10/10 Excellent

Alexandra

A woman at a counter in a restaurant with a sign above reading "The Bay Tree Restaurant."

Bay Tree Hotel

Burford

10/10 Excellent

Cathy

A narrow street with parked cars, a bench, and a building with a 'No Smoking' sign.

The Lamb Inn

Burford

10/10 Excellent

Sandra

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 $108 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 Cotswold Country Park and Beach. 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.

Winson Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winson vacation rentals

1. The Lakes By YOO

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

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

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

5. 1 bedroom accommodation in Chedworth, near Cheltenham

6. Strozzi Palace Suites by Mansley

7. Crescent Place by Mansley

8. Grey's Court Cottages

9. The Haybarn Banham Cottages

10. Molly's Bit

11. Beechwood Cottage Banham Cottages

12. Cotswold Townhouse - Adults Only

13. Sycamore Cottage Banham Cottages

14. Portland Apartments

15. The Stables Banham Cottages

16. Bourton on the Water Country Chic Authentic Cottage

17. George Apartments

18. 21 Montpellier Terrace

19. Old Fleece Apartments

20. The Clock Tower

Find vacation rentals that suit your style

Top Winson Hotel Reviews

Wild Thyme & Honey

10/10 Excellent

Find out more about Winson

Winson vacation rentals: An excellent choice for every season

How to find incredible deals on Winson rentals

Frequently Asked Questions

Can I find a vacation rental in Winson?

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

What’s there to see and do in Winson?

What’s a vacation rental in Winson like?