Winson Vacation Rentals from $101: Search Short-Term Rentals

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Our top choices for Winson vacation rentals

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

1. Strozzi Palace Suites by Mansley

Cheltenham

Bridget

$88 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

2. Crescent Place by Mansley

Cheltenham

Lisa

$97 nightly

Oct 1 - Oct 2

Total with taxes and fees

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

3. George Apartments

Broadway

Leah

$134 nightly

Sep 20 - Sep 21

Total with taxes and fees

A beige building with a black door, a small set of steps, and two potted plants.

4. Portland Apartments

Cheltenham

Helen

$131 nightly

Oct 12 - Oct 13

Total with taxes and fees

A cozy room with a bed, a small table, a sofa, and a view of the outdoors.

5. The Coach House and The Stable

Stroud

Tania

$84 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern living room with a glass dining table set for six, green upholstered chairs, a brown sofa, a flat-screen TV, and a large window with a view of a building.

6. High Life Luxury Serviced Apartments

South Swindon

Frances

A modern living room with a dining area, a staircase, and a view of the outside.

7. Suite Life Serviced Apartments

South Swindon

Mark

$307 nightly

Sep 24 - Sep 25

Total with taxes and fees

A spacious living room with a leather sofa, a coffee table with a tray, and a wooden cabinet.

8. The Judges Lodgings Boutique Hotel

Gloucester

Andrew

$173 nightly

Sep 15 - Sep 16

Total with taxes and fees

A row of traditional stone buildings with a shop on the corner.

9. The Shop Cotswold Apartment Sleeps 2

Cirencester

Frank

$184 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern apartment with a living room, dining area, and kitchen. There is a flat-screen TV, a glass coffee table with a vase, and a red rug. The kitchen has grey cabinets and a built-in oven.

10. Elliot Oliver - Stylish Loft Style 2 Bedroom Apartment With Parking

Gloucester

Jacek

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

11. Old Fleece Apartments

Stroud

Alan

$89 nightly

Sep 13 - Sep 14

Total with taxes and fees

A wooden table with a vase of tulips, two glasses, and a loaf of bread.

12. The Cowshed Banham Cottages

Bourton-on-the-Water

Pratigya

$616 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

13. The Lakes By YOO

Lechlade

"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...

Josh

$207 nightly

Oct 12 - Oct 13

Total with taxes and fees

A stone cottage with a thatched roof, a small garden, and a wooden bench.

14. Mayfly Cottage

Cirencester

Ashril

$588 nightly

Sep 19 - Sep 20

Total with taxes and fees

A hotel room with a bed, a sofa, a small table, a chair, a desk, a lamp, a picture on the wall, and a window with blinds.

15. The Cozy Apartment

Gloucester

Matt

$111 nightly

Oct 4 - Oct 5

Total with taxes and fees

A white door with a wreath, a mailbox, and a number plate indicating '10'.

16. Cotswold Stay

Burford

Jayne

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

17. Grey's Court Cottages

Southrop

$514 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern living room with a flat-screen TV, wooden entertainment unit, a coffee table with snacks, a sofa with a yellow pillow, and a balcony with outdoor seating.

18. Elliot Oliver - 2 Bedroom Garden Apartment With Parking

Cheltenham

Kate

A compact kitchen with a washing machine, microwave, and stove.

19. Nelson Serviced Apartments

Gloucester

Tim

$111 nightly

Oct 4 - Oct 5

Total with taxes and fees

A compact living space with a kitchenette, two sofas, a dining table, and a small garden view.

20. Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

Gloucester

Andrew

$130 nightly

Sep 17 - Sep 18

Total with taxes and fees

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Top Winson Hotel Reviews

Leonardo Hotel Cheltenham

8/10 Good

"Breakfast and helpful receptionist very good. I booked this hotel as it had an EV charger. Our neighbours in the room nextdoor were a bit noisy, but no fault of the hotel. The duvets were too warm for a summer's day, and only read the bit about asking for a sheet too late."

Stratton House Hotel & Spa

8/10 Good

"The outside of the hotel and the public areas are very cute and well maintained. Tons of character. The room itself was ok. The carpet was very worn and the desk chair a bit ratty. But the bathroom is very nice with both a claw foot tub and a walk in shower. Easy 25 minute walk into town. Free parking. Would stay again but hopefully in a different room."

Village Hotel Swindon

8/10 Good

"It was a great place to stay with free parking , in house pub , gym ( requires extra payment), swimming pool( also requires payment over the room charges). Rooms were big, comfortable, with comfortable beds, Wi-Fi, TV , and a great shower. All in all if you are not looking for extreme refinement it is a great place to stay"

Gloucester Robinswood Hotel by Sunday

8/10 Good

"We had an enjoyable time staying here. A pit stop on the way to another venue. Room was a good size and the bed was comfortable. The sauna and steam room were excellent. The staff very pleasant, helpful and smiley. We didn’t try any food here as we went out. Would stay here again."

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winson in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Room 1

Check prices for these dates

Our top choices for Winson vacation rentals

1. Strozzi Palace Suites by Mansley

2. Crescent Place by Mansley

3. George Apartments

4. Portland Apartments

5. The Coach House and The Stable

6. High Life Luxury Serviced Apartments

7. Suite Life Serviced Apartments

8. The Judges Lodgings Boutique Hotel

9. The Shop Cotswold Apartment Sleeps 2

10. Elliot Oliver - Stylish Loft Style 2 Bedroom Apartment With Parking

11. Old Fleece Apartments

12. The Cowshed Banham Cottages

13. The Lakes By YOO

14. Mayfly Cottage

15. The Cozy Apartment

16. Cotswold Stay

17. Grey's Court Cottages

18. Elliot Oliver - 2 Bedroom Garden Apartment With Parking

19. Nelson Serviced Apartments

20. Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

Find vacation rentals that suit your style

Top Winson Hotel Reviews

Leonardo Hotel Cheltenham

Hatherley Manor Hotel & Spa

Queens Hotel Cheltenham

Hotel Indigo Gloucester The Forum By IHG

Stratton House Hotel & Spa

The Lygon Arms

Village Hotel Swindon

Kings Head

Gloucester Robinswood Hotel by Sunday

Find out more about Winson

Frequently asked questions