Winstone Vacation Rentals from CA $76: Short-Term Rentals for 2026

Q: What are some of the best vacation home rentals in Winstone?

Spacious, Cosy Cotswolds Farmhouse with Annex : Visitors like this Winstone vacation home rental. It offers a fireplace, a hot tub, and laundry facilities to help you feel perfectly comfortable 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.

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

In two months

In three months

In four months

Our top choices for Winstone vacation rentals

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

1. The Coach House and The Stable

Stroud

Tania

CA $141 total

includes taxes & fees

Nov 15 - Nov 16

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

2. Old Fleece Apartments

Stroud

Charlotte

CA $149 total

includes taxes & fees

Nov 15 - Nov 16

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

3. Crescent Place by Mansley

Cheltenham

Simon

CA $141 total

includes taxes & fees

Nov 29 - Nov 30

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

Cheltenham

Roy

CA $136 total

includes taxes & fees

Nov 22 - Nov 23

5. Relaxing Retreat in Cheltenham

Cheltenham

Wilbert M.

CA $122 total

includes taxes & fees

Nov 10 - Nov 11

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

6. The Judges Lodgings Boutique Hotel

Gloucester

Andrew

CA $267 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Poulton

Walter

CA $147 total

includes taxes & fees

Nov 15 - Nov 16

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

8. The Lakes By YOO

Lechlade

Mathew

CA $331 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with a bed, a desk, a chair, a TV mounted on the wall, and a kitchenette in the background.

9. Spa Court

Cheltenham

Paul

CA $127 total

includes taxes & fees

Nov 10 - Nov 11

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.

10. The Cozy Apartment

Gloucester

Matt

CA $187 total

includes taxes & fees

Nov 15 - Nov 16

A neatly made bed with a quilted headboard, two bedside tables with lamps, and a wardrobe to the right.

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

Cirencester

Cheri L.

CA $256 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a large bed, a checkered armchair, a decorative wall panel, and a window.

12. Grigshot Apartment

Stroud

Gregory

CA $255 total

includes taxes & fees

Nov 9 - Nov 10

A living room with a fireplace, a chandelier, a dining area, and a kitchen in the background.

13. Portland Apartments

Cheltenham

Helen

CA $243 total

includes taxes & fees

Nov 23 - Nov 24

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

14. 21 Montpellier Terrace

The Suffolks

Tarun

CA $353 total

includes taxes & fees

Nov 11 - Nov 12

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

15. George Apartments

Broadway

Peter

CA $244 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Gloucester

Richard

CA $168 total

includes taxes & fees

Dec 6 - Dec 7

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

17. 1 bedroom accommodation in Chedworth, near Cheltenham

Chedworth, near Cheltenham

Nigel Coote

CA $598 total

includes taxes & fees

Nov 20 - Nov 21

A spacious living room with a fireplace, comfortable seating, a dining area, and large windows offering a view of the outdoors.

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

Montpellier

Carol W.

CA $463 total

includes taxes & fees

Nov 16 - Nov 17

A stone fireplace with a wood-burning stove, a stack of firewood to the left, and a television on a wooden stand to the right.

19. Cosy Cotswold Stone Cottage with wood burner and 2.5 bathrooms

Winchcombe

martyn s.

CA $336 total

includes taxes & fees

Dec 1 - Dec 2

A brick house with a patio, a bench, and a table with chairs.

20. The Lodge at Bredon's Norton

Tewkesbury

CA $185 total

includes taxes & fees

Dec 7 - Dec 8

View all properties

Find vacation rentals that suit your style

Top Winstone Hotel Reviews

A wooden dining table with a bottle of champagne, a glass of white wine, a plate with food, and a vase with flowers.

The Falcon Painswick

Stroud

10/10 Excellent

Peter

The Colesbourne Inn

Cheltenham

10/10 Excellent

Janaya

A stone building with multiple windows and a signboard, likely a hotel or inn, with a well-maintained lawn and a paved driveway.

The Royal George Birdlip by Greene King Inns

Gloucester

10/10 Excellent

Peter

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 bedroom with a large bed, multiple pillows, a wooden nightstand, a mirror, and a textured wall.

Beaumont House

Cheltenham

10/10 Excellent

Beaumont House is a beautiful Bed & Breakfast on the outskirts of Cheltenham. On arrival we were shown around the facilities and offered a glass of Prosecco. Our room was small, which was stated on the website, but had everything we needed for one night. We usually sleep with the window open but as the room was below ground level we didn't feel comfortable doing so but apart from that everything was excellent. The breakfast menu was extensive and the food freshly cooked and served with a...

Michael

A patio with lounge chairs and a glass-enclosed area.

Stratton House Hotel & Spa

Cirencester

10/10 Excellent

paul

An indoor swimming pool with a hot tub, surrounded by lounge chairs and a brick wall with a green wall feature.

Holiday Inn Gloucester-Cheltenham by IHG

Gloucester

10/10 Excellent

One of nicest bunch of staff have met at a hotel. Very hardworking, diligent and actually care about their guests. Rooms were clean and comfortable and the pool and gym were excellent. Only issue was on checkin as it took a very long time as a couple guests were having payment and suite issues. Parking is close by, food in restaurant was perfect and breakfast had a lot of choices. This hotel takes good allergies super serious and lots of dairy gluten free options available- we were sad to...

Thomas

A stone building with a sign reading "Masons Arms."

The Masons Arms

Cirencester

10/10 Excellent

Tibor

A Holiday Inn Express building with a covered entrance and a visible sign.

Holiday Inn Express Gloucester - South by IHG

Gloucester

10/10 Excellent

Karen Jayne

A long wooden dining table with chairs, a vase with flowers, and wine bottles in a brick-walled room with a vaulted ceiling.

Kings Head

Cirencester

10/10 Excellent

Sheryl Geraldine

Find out more about Winstone

Everything you need to know about Winstone 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 Winstone 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 Winstone vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winstone vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winstone. 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 Winstone 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 Winstone vacation rentals we have selected for you start as low as CA $76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winstone rentals

At Expedia, we put the best Winstone 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 Winstone 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 Winstone 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 Winstone. 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

Are there vacation rentals in Winstone?

Yes, we offer vacation rentals near top attractions in Winstone, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Winstone?

Spacious, Cosy Cotswolds Farmhouse with Annex: Visitors like this Winstone vacation home rental. It offers a fireplace, a hot tub, and laundry facilities to help you feel perfectly comfortable 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.

What can I see and do in Winstone?

While exploring the area, visit family-friendly sights like Cotswold Farm Park, or get outside and enjoy nature at Minchinhampton Common. Cirencester Church and Chedworth Roman Villa are a couple of places you'll find in the larger area.

What are vacation rentals like in Winstone?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Winstone. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

Winstone Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winstone vacation rentals

1. The Coach House and The Stable

2. Old Fleece Apartments

3. Crescent Place by Mansley

4. Strozzi Palace Suites by Mansley

5. Relaxing Retreat in Cheltenham

6. The Judges Lodgings Boutique Hotel

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

8. The Lakes By YOO

9. Spa Court

10. The Cozy Apartment

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

12. Grigshot Apartment

13. Portland Apartments

14. 21 Montpellier Terrace

15. George Apartments

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

17. 1 bedroom accommodation in Chedworth, near Cheltenham

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

19. Cosy Cotswold Stone Cottage with wood burner and 2.5 bathrooms

20. The Lodge at Bredon's Norton

Find vacation rentals that suit your style

Top Winstone Hotel Reviews

The Falcon Painswick

10/10 Excellent

Find out more about Winstone

Winstone vacation rentals: An excellent choice for every season

How to find incredible deals on Winstone rentals

Frequently Asked Questions

Are there vacation rentals in Winstone?

What are some of the best vacation home rentals in Winstone?

What can I see and do in Winstone?

What are vacation rentals like in Winstone?

Explore a world of travel with Expedia