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Winstone Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winstone vacation rentals

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

1. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.2 out of 10, Wonderful, (135 reviews)
"Room had our stay in Cheltenham, would definitely recommend and stay again."
United Kingdom
Lisa
$96 nightly
The price is $115
Sep 13 - Sep 14
Total with taxes and fees
Crescent Place by Mansley
A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

2. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (242 reviews)
"I had a lovely stay here with my mum. We had the siena suite and it was exceptionally clean and as per the photos. Was really nice to have the terrace and kitchenette aswell. We recieved a warm welcome from friendly staff who helped us up to the suite with our bags. Great central location and well priced too. Would definitely recommend!"
United Kingdom
Bridget
$93 nightly
The price is $111
Oct 4 - Oct 5
Total with taxes and fees
Strozzi Palace Suites by Mansley
A cozy room with a bed, a small table, a sofa, and a view of the outdoors.

3. The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
8.8 out of 10, Excellent, (46 reviews)
"Great stay "
United Kingdom
Tania
$84 nightly
The price is $101
Sep 27 - Sep 28
Total with taxes and fees
The Coach House and The Stable
A large stone building with multiple windows and a prominent tower.

4. 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
$82 nightly
The price is $99
Sep 6 - Sep 7
Total with taxes and fees
Old Fleece Apartments
A beige building with a black door, a small set of steps, and two potted plants.

5. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (154 reviews)
"Fantastic accommodation."
United Kingdom
Helen
$129 nightly
The price is $155
Sep 28 - Sep 29
Total with taxes and fees
Portland Apartments
A spacious living room with a leather sofa, a coffee table with a tray, and a wooden cabinet.

6. The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel
3.5 star property
Gloucester
9.0 out of 10, Wonderful, (17 reviews)
"The apartment was brilliant grrat bathrooms and the bed was amazingly comfortable, the kitch area was brilliant "
United Kingdom
Andrew
$161 nightly
The price is $193
Sep 13 - Sep 14
Total with taxes and fees
The Judges Lodgings Boutique Hotel
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.

7. The Cozy Apartment

The Cozy Apartment
2.0 star property
Gloucester
7.6 out of 10, Good, (19 reviews)
"Suited our needs perfectly for our short stay to take part in Gloucester half marathon. "
United Kingdom
Matt
$111 nightly
The price is $134
Sep 13 - Sep 14
Total with taxes and fees
The Cozy Apartment
A wooden picnic table with a tray of green and white cups and a small potted plant.

8. Swallow Studio

Swallow Studio
3.0 star property
Cheltenham
$451 nightly
The price is $541
Sep 8 - Sep 9
Total with taxes and fees
Swallow Studio
A breakfast setup with croissants and orange juice by a window overlooking a parking lot and buildings.

9. Elliot Oliver - Loft Style 2 Bedroom Apartment With Parking In The Docks

Elliot Oliver - Loft Style 2 Bedroom Apartment With Parking In The Docks
3.5 star property
Gloucester
9.6 out of 10, Exceptional, (28 reviews)
"The location is excellent only a short walk to some brilliant restaurants and the city centre "
United Kingdom
Geoffrey
Elliot Oliver - Loft Style 2 Bedroom Apartment With Parking In The Docks

10. Prime Location I Comfortable Spacious

Prime Location I Comfortable Spacious
Cirencester
Prime Location I Comfortable Spacious
A modern interior with a wooden deck overlooking a pool and water.

11. The Lakes By YOO

The Lakes By YOO
5.0 star property
Lechlade
8.6 out of 10, Excellent, (44 reviews)
"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...
United Kingdom
Josh
$210 nightly
The price is $252
Oct 5 - Oct 6
Total with taxes and fees
The Lakes By YOO
A neatly made bed with a quilted headboard, two bedside tables with lamps, and a wardrobe to the right.

12. 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)
"Comfortable and lovely place to stay. Close to walk to dinner or enjoy the town. The washing machine was full of wet clothes so we didn’t get to use that. We found parking and as these small towns go, it was close to the apartment. Very quiet and clean good communication with owner. "
United States
Jan
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.

13. George Apartments

George Apartments
2.0 star property
Broadway
9.4 out of 10, Exceptional, (52 reviews)
"Absolutely loved staying here. Air Conditioning was truly a luxury in the heat wave! Amazing location too."
United States
Leah
$144 nightly
The price is $173
Sep 9 - Sep 10
Total with taxes and fees
George Apartments
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, (23 reviews)
"Very relaxed and quiet location. Cottage well appointed."
United States
Nigel Coote
$699 nightly
The price is $699
Oct 5 - Oct 6
Total with taxes and fees
1 bedroom accommodation in Chedworth, near Cheltenham
A stone wall with a metal gate, a stone building with a tiled roof, and a grassy lawn.

15. 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, (48 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
$114 nightly
The price is $114
Sep 20 - Sep 21
Total with taxes and fees
Recently converted self-contained apartment with garden in Cotswold village
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

Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
3.5 star property
Gloucester
8.2 out of 10, Very Good, (22 reviews)
"Well equipped and comfortable apartment right in the centre of Gloucester. Easy walk to shops and restaurants and to Docks for outlet shopping."
United Kingdom
Andrew
$129 nightly
The price is $155
Oct 1 - Oct 2
Total with taxes and fees
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
A spacious living room with a fireplace, comfortable seating, a dining area, and large windows offering a view of the outdoors.

17. 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.
$314 nightly
The price is $314
Sep 7 - Sep 8
Total with taxes and fees
Beautiful & spacious Regency apt in centre Cheltenham, free parking
A wooden house with a garden, a wooden fence, and a welcome sign.

18. Wellinghill Lodge

Wellinghill Lodge
3.0 star property
Cheltenham
$425 nightly
The price is $510
Oct 5 - Oct 6
Total with taxes and fees
Wellinghill Lodge
A compact kitchen with a washing machine, microwave, and stove.

19. Nelson Serviced Apartments

Nelson Serviced Apartments
3.5 star property
Gloucester
6.6 out of 10, (34 reviews)
"Great apartment at Friary but our room was on 3rd floor with no elevator which could be a struggle for some. "
United States
Tim
$112 nightly
The price is $134
Sep 27 - Sep 28
Total with taxes and fees
Nelson Serviced Apartments
A traditional stone cottage with a garden, a pathway, and parked cars.

20. 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, (3 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.
$356 nightly
The price is $356
Sep 6 - Sep 7
Total with taxes and fees
Rosemary Cottage, cosy with a real fire just 5 minute walk from Arlington Row
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 Winstone Hotel Reviews

Queens Hotel Cheltenham

Queens Hotel Cheltenham

8/10 Good
"The rooms were large and comfortable, I liked the coffee machine. The l"
Alastair 1-night trip
Posted 9 hours ago
Queens Hotel Cheltenham

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, 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 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 low season months. For more hustle and bustle, you may prefer to visit Winstone 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 $99 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 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?

Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub : Visitors like this Winstone vacation home rental. It offers a fireplace, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Pittville Park. 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.