Photo by Bob Embleton

Upton St. Leonards Holiday Rentals

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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 S$769
includes taxes & fees
19 Dec - 20 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 S$145
includes taxes & fees
21 Dec - 22 Dec
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 S$238
includes taxes & fees
15 Dec - 16 Dec
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 S$211
includes taxes & fees
16 Dec - 17 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 S$144
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 S$130
includes taxes & fees
14 Dec - 15 Dec
The Coach House and The Stable
Balcony
Weir Cottage

Weir Cottage

Weir Cottage
3.5 star property
Cheltenham
The price is S$2,198
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 S$215
includes taxes & fees
14 Dec - 15 Dec
The Judges Lodgings Boutique Hotel
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 S$1,769
includes taxes & fees
21 Dec - 22 Dec
Suncroft
Exterior
The Snicket

The Snicket

The Snicket
3.0 star property
Cheltenham
The Snicket
Private kitchen
The Old Swan

The Old Swan

The Old Swan
3.0 star property
Malmesbury
The price is S$2,373
includes taxes & fees
4 Jan - 5 Jan, 2026
The Old Swan
Outdoor dining
2 Bed House - Sleeps 6 - Garden, Pets, Parking

2 Bed House - Sleeps 6 - Garden, Pets, Parking

2 Bed House - Sleeps 6 - Garden, Pets, Parking
3.5 star property
Cheltenham
8.0 out of 10, Very good, (1)
"Great location, cottage was cosy and spacious with good amenities. Dog friendly and we had an enjoyable stay. Good restaurants in the area too "
United Kingdom
Tina
The price is S$406
includes taxes & fees
22 Dec - 23 Dec
2 Bed House - Sleeps 6 - Garden, Pets, Parking
Fridge, oven, stovetop, cookware/dishes/utensils
The Skydeck

The Skydeck

The Skydeck
3.0 star property
Cirencester
The price is S$2,434
includes taxes & fees
3 Jan - 4 Jan, 2026
The Skydeck
Interior
Cotswold View

Cotswold View

Cotswold View
3.5 star property
Cheltenham
The price is S$982
includes taxes & fees
17 Dec - 18 Dec
Cotswold View
Interior
Tickmorend Farm

Tickmorend Farm

Tickmorend Farm
3.5 star property
Stroud
The price is S$4,314
includes taxes & fees
17 Dec - 18 Dec
Tickmorend Farm
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 Upton St. Leonards Hotel Reviews

Queens Hotel Cheltenham

Queens Hotel Cheltenham

10/10 Excellent
"A pleasant stay at this hotel, we were provided with early check-in and a free upgrade to an executive room. Restaurant food was good and staff were friendly. We found our room fairly hot so had to turn down the radiators. The room had free drinks, which was a bonus."
PHILIP 2-night trip
Posted 3 days ago
Queens Hotel Cheltenham

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’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.