Photo by Bob Embleton

Upton St. Leonards Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Upton St. Leonards holiday rentals

Fridge, electric kettle, toaster, cookware/dishes/utensils
Little Noo

Little Noo

Little Noo
3.0 star property
Gloucester
The price is HK$3,828
HK$4,593 total
includes taxes & fees
15 Dec - 16 Dec
Little Noo
In-room safe, individually decorated, individually furnished, desk
Crescent Place by Mansley

Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (88)
"Good location, clean and nice rooms. "
United Kingdom
Jessica
The price is HK$738
HK$885 total
includes taxes & fees
4 Jan - 5 Jan 2026
Crescent Place by Mansley
Front of property
Portland Apartments

Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (135)
"•Great Location •Apartment immaculate •Tastefully decorated •Friendly hosts •A luxurious home from home •Highly recommend •Complimentary Tea, Coffee, Milk, Orange Juice and Croissants "
United Kingdom
Debra
The price is HK$1,146
HK$1,376 total
includes taxes & fees
12 Jan - 13 Jan 2026
Portland Apartments
48-inch flat-screen TV with digital channels, TV
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception

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, (21)
"Nice, central location. Quays nearby, so plenty of choices to eat/drink as well as the city centre being right there. Apartment was spacious, clean, recently refurbished by the look of it. Bed was comfortable, plenty of space in the apartment, nice kitchen and bathroom. "
United Kingdom
Robert
The price is HK$1,103
HK$1,324 total
includes taxes & fees
14 Dec - 15 Dec
Friary House Serviced Apartments by Roomsbooked - 24Hr Reception
Reception
Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (199)
"Excellent suites and great location!"
United Kingdom
Barrie
The price is HK$722
HK$867 total
includes taxes & fees
11 Jan - 12 Jan 2026
Strozzi Palace Suites by Mansley
Desk, blackout curtains, iron/ironing board, free WiFi
Spa Court

Spa Court

Spa Court
3.0 star property
Cheltenham
7.4 out of 10, Good, (40)
"Very good, well equipped apartment in a central location."
Ireland
paul
Spa Court
1 bedroom
The Coach House and The Stable

The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
9.0 out of 10, Wonderful, (41)
"Great stay "
United Kingdom
Tania
The price is HK$651
HK$781 total
includes taxes & fees
21 Dec - 22 Dec
The Coach House and The Stable
Outdoor pool, a heated pool
HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY

HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY

HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY
FERNEY
10.0 out of 10, Exceptional, (74)
"Beautifully designed and appointed with high class facilities and beautiful design."
United Kingdom
Christopher B.
HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY
1 bedroom, bed sheets
Shepherds Hut in the Cotswolds

Shepherds Hut in the Cotswolds

Shepherds Hut in the Cotswolds
Stanway
10.0 out of 10, Exceptional, (6)
"Had a lovely stay, the place was clean and tidy and the surroundings were peaceful and quiet. The next time I’m heading to the area I will definitely look to book this place again."
United Kingdom
Lain H.
The price is HK$1,294
HK$1,471 total
includes taxes & fees
11 Jan - 12 Jan 2026
Shepherds Hut in the Cotswolds
Interior
Luxury Cosy Cottage In Magical Bibury

Luxury Cosy Cottage In Magical Bibury

Luxury Cosy Cottage In Magical Bibury
Bibury
9.0 out of 10, Wonderful, (13)
"Great location to my friend’s house. "
United Kingdom
April H.
Luxury Cosy Cottage In Magical Bibury
Fridge, microwave, oven, stovetop
Two bedroom holiday cottage with garden and off-street parking, Bourton-on-the-Water - North House

Two bedroom holiday cottage with garden and off-street parking, Bourton-on-the-Water - North House

Two bedroom holiday cottage with garden and off-street parking, Bourton-on-the-Water - North House
Bourton-on-the-Water
9.8 out of 10, Exceptional, (51)
"We had a great time. The host was amazing and communicated very efficiently. Thank you very much and we look forward to staying again soon"
United States
Anonymous traveller
Two bedroom holiday cottage with garden and off-street parking, Bourton-on-the-Water - North House
Property grounds
Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub

Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub

Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub
North Nibley
10.0 out of 10, Exceptional, (142)
"A lovely spacious house that is luxuriously furnished. We had a wonderful family weekend enjoying the house and the local area. We can thoroughly recommend this property. "
United Kingdom
Gill S.
Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub
Balcony
Weir Cottage

Weir Cottage

Weir Cottage
3.5 star property
Cheltenham
The price is HK$10,937
HK$13,124 total
includes taxes & fees
17 Dec - 18 Dec
Weir Cottage
Private kitchen
The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel
2.0 star property
Gloucester
8.4 out of 10, Very good, (7)
"The location was great and the area quiet. Convenient to train and bus, grocery, and local interests. Property was ok in cleanliness (white grout and subway tile require a LOT of maintenance) and the modern updates were poorly installed. Far too many bric-a-brac to keep dusted. Comfortable and spacious. "
United States
Erin
The price is HK$548
HK$1,283 total
includes taxes & fees
14 Dec - 15 Dec
The Judges Lodgings Boutique Hotel
Exterior
The Little House on Gumstool Hill

The Little House on Gumstool Hill

The Little House on Gumstool Hill
Tetbury
8.8 out of 10, Excellent, (30)
"Very convenient place to stay and visit Cotswolds."
France
David C.
The price is HK$563
HK$1,173 total
includes taxes & fees
14 Dec - 15 Dec
The Little House on Gumstool Hill
Desk, bed sheets
Vernon Place Accommodation

Vernon Place Accommodation

Vernon Place Accommodation
3.0 star property
Cheltenham
10.0 out of 10, Exceptional, (2)
" Excellent quiet location, close to the high street with lots of options for eating out.Well maintained property, nice and clean. Overall 5/5 Single traveller, business trip."
United Kingdom
Anonymous traveller
Vernon Place Accommodation
Private kitchen
Elliot Oliver- Charming 1 Bed Apartment

Elliot Oliver- Charming 1 Bed Apartment

Elliot Oliver- Charming 1 Bed Apartment
4.0 star property
Gloucester
10.0 out of 10, Exceptional, (7)
"Excellent apartment, very central and parking is a bonus. Plenty of eateries nearby and a few minutes walk into the city centre for shopping & sightseeing 😊 "
United Kingdom
Peter
Elliot Oliver- Charming 1 Bed Apartment
Private kitchen
Cheltenham Country Retreats

Cheltenham Country Retreats

Cheltenham Country Retreats
3.5 star property
Cheltenham
Cheltenham Country Retreats
Exterior
The Cozy Apartment

The Cozy Apartment

The Cozy Apartment
2.0 star property
Gloucester
7.6 out of 10, Good, (19)
"Suited our needs perfectly for our short stay to take part in Gloucester half marathon. "
United Kingdom
Matt
The Cozy Apartment
Fridge, dishwasher, electric kettle, toaster
Suncroft

Suncroft

Suncroft
3.0 star property
Cheltenham
The price is HK$8,801
HK$10,562 total
includes taxes & fees
17 Dec - 18 Dec
Suncroft
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upton St. Leonards Hotel Reviews

De Vere Cotswold Water Park

De Vere Cotswold Water Park

10/10 Excellent
"Excellent "
Amy 2-night trip
Posted 4 days ago
De Vere Cotswold Water Park

Find out more about Upton St. Leonards

Search for holiday rentals in Upton St. Leonards on Expedia! You can easily find your home rentals, villas, holiday apartments in Upton St. Leonards using one of the methods below:

  • View our selection of featured holiday rentals in Upton St. Leonards
  • Use the map to find apartments and other holiday homes in the Upton St. Leonards neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upton St. Leonards while they last

Look no further and take a look at our great range of rental properties in Upton St. Leonards!

Frequently asked questions

Can I find holiday rentals in Upton St. Leonards?

Yes, there are holiday rentals close to the most popular sights in Upton St. Leonards, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Upton St. Leonards speak positively about the countryside and restaurants in this destination. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Upton St. Leonards has to offer?

Comfy modern townhouse/w free parking & garden, newly refurbished, self catering: This holiday home rental outside of Upton St. Leonards offers a fireplace, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What’s there to see and do in Upton St. Leonards?

While exploring the area, visit family-friendly sights like Greyfriars, or get outside and enjoy nature at Pittville Park. Prinknash Abbey and Gloucester Quays are a couple of places you'll find in the wider area.

What’s a holiday rental in Upton St. Leonards like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Upton St. Leonards. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family gatherings.