Cheltenham Holiday Rentals

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Holiday Rentals in Cheltenham

2 bedrooms, iron/ironing board, free WiFi, bed sheets
Characterful 16th Century Cottage, off street parking, 2 Min Walk to Village!
10.0 out of 10, Exceptional, (103)
"If you want to feel like you are starring in your own movie in a charming English village, book Well Cottage! The cottage is situated in the most perfect location. I did not have a car. So I spent mornings on long walks and then a nice lunch in the village. Then "home" to Well Cottage to rest my back in comfort, have a nice hot bath and then an evening out or reading in front of the fire. I slept so deeply( beautiful linens) in a very cozy bed. The street just behind the village and the...
Characterful 16th Century Cottage, off street parking, 2 Min Walk to Village!
Fridge, microwave, oven, stovetop
Lovely quirky cotswold cottage (Old Telephone Exchange)
10.0 out of 10, Exceptional, (23)
"It was just right for the 3 of us. Its situation, within walking distance of shops, pubs, etc. was excellent. There was lots of dog walks in open countryside......... she loved it! One minor grouse - the cooker was qite complicated, and the instructions in the welcome pack didn't fit the exact model of cooker. Otherwise, we loved Exchange cottage, and we loved Northleach........ we'll be back"
Lovely quirky cotswold cottage (Old Telephone Exchange)
Property grounds
Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment
4.0 star property
10.0 out of 10, Exceptional, (12)
"the appartment is very clean and comfortable. the location near city centre is very good. "
Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment
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Smart TV, fireplace, ping pong, books
elegant period 5 bed house close to town centre,sleeps 15
10.0 out of 10, Exceptional, (4)
"This pictures honestly don’t do this place justice… a stunning and spacious home with some beautiful details. Super clean, decorated beautifully with towels, everything you could need in the kitchen, lovely beds, shower gel… The host was extremely helpful after having some issues with a different site and switching over to vrbo. Great communication from start to finish with a super friendly and helpful person! A great central location on a safe road with registered parking, plenty of things...
The price is NZ$779
per night
16 May - 17 May
elegant period 5 bed house close to town centre,sleeps 15
Bar (on property)
NEW LISTING - Chic Apt in Central Cheltenham Free Permit Parking
10.0 out of 10, Exceptional, (21)
"My overall experience was wonderful. Any questions I had were answered in a timely manner. The only issues I had to work around were most mirrors in the place were placed rather high for my 5'0 stature 😄. The living room/dinning area was perfect for when my local friends came for a visit. I would definitely recommend this place for a single or a couple."
NEW LISTING - Chic Apt in Central Cheltenham Free Permit Parking
Exterior
Enchanting Grade II listed,Log Burner,allocated parking,town centre but secluded
10.0 out of 10, Exceptional, (144)
"This property is simply gorgeous. The location is superb and as described in the listing. The host was a great communicator and was happy to offer dinner location suggestions. Highly recommend booking here for your stay in this glorious part of the Cotswolds."
Enchanting Grade II listed,Log Burner,allocated parking,town centre but secluded
Property grounds
Cosy Cotswold Cottage - Penny Cottage - pet friendly - sleeps 2
10.0 out of 10, Exceptional, (2)
"Cottage is in the middle of town, so everything was so close. Quiet place with everything you need for a comfortable stay."
Cosy Cotswold Cottage - Penny Cottage - pet friendly - sleeps 2
Smart TV, Netflix, streaming services
The Little House, Luxury Cotswolds Stunning Views
10.0 out of 10, Exceptional, (4)
"Had a fantastic short holiday and this lovely cottage. Very spacious for a one bedroom. The cottage is beautifully presented with some quirky decor touches, which make it feel very individual and not at all like a generic rental. It has a really lovely atmosphere. The garden is enclosed so fantastic for the dog. There are some really nice places to visit not too far away. Communication with owners was also excellent. They did all they could to make staying their property as enjoyable as...
The Little House, Luxury Cotswolds Stunning Views
Romantic Apartment
Church Suite
4.0 star property
10.0 out of 10, Exceptional, (1)
Church Suite
Exterior
Lovely Cotswold holiday cottage within walking distance of restaurants/shops
10.0 out of 10, Exceptional, (72)
"Exactly as described. We had one maintenance issue and it was resolved almost immediately."
Lovely Cotswold holiday cottage within walking distance of restaurants/shops
Exterior
Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe.
10.0 out of 10, Exceptional, (63)
"I spent a week at No. 6 Vineyard and I found the host to be very helpfu. The property was well stocked with everything needed within reason, featured a great, bright kitchen and a nice back garden. Location was excellent."
Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe.
Fridge, microwave, oven, stovetop
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water
9.8 out of 10, Exceptional, (15)
"Family (5 + dog) enjoyed the long easter weekend in this house. It was pretty, well equipped, and we had a great time."
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water
Apartment, 1 Bedroom (Prestbury Suite) | Private kitchen
Portland Apartments
3.5 star property
9.8 out of 10, Exceptional, (105)
"Fabulous hotel. The little extras were very welcome too!"
The price is NZ$250
per night
27 May - 28 May
Portland Apartments
Exterior
Period cottage in idyllic riverside location in prime Cotswolds village
9.8 out of 10, Exceptional, (34)
"Splendid property, perfectly situated for countryside walks and proximity to quintessential Cotswolds towns. Very comfortable beds, steep staircase so may not be appropriate for older people, wonderful spot!"
Period cottage in idyllic riverside location in prime Cotswolds village
Fridge, microwave, oven, stovetop
The Granary is in a rural location, perfect for families, couples and pets.
9.8 out of 10, Exceptional, (28)
"Beautiful and spacious cottage with fully stocked kitchen that fit our family of four perfectly. Warm and welcoming hosts. Welcome package and guides were appreciated. Close to several activities / attractions across Cotswolds and within ten minutes of a grocery store. Kids had a blast playing in the lovely gardens and playing fetch with the friendly dog. We would absolutely return should we ever find ourselves in the Cotswolds again, and would recommend this stay to everyone."
The Granary is in a rural location, perfect for families, couples and pets.
Property grounds
Holiday Cottage in Winchcombe Cotswolds. Sleeps 6 in 3 bedrooms.
9.8 out of 10, Exceptional, (27)
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Holiday Cottage in Winchcombe Cotswolds. Sleeps 6 in 3 bedrooms.
Reception
Strozzi Palace Suites by Mansley
4.0 star property
9.6 out of 10, Exceptional, (150)
"First time booking an apartment and no regrets. Large main room and bedroom as well as excellent bathroom. Everything you need to either eat in the apartment or take advantage of the multitude of bars, restaurants and cafes in the Town centre. Large screen smart TV with a the usual apps already installed. Full crockery and cutlery with coffee machine, microwave, kettle and large fridge with freezer compartment. Communication from Roy the manager was superb and ensured everything went smoothly...
The price is NZ$188
per night
19 May - 20 May
Strozzi Palace Suites by Mansley
TV, fireplace, books
WORK FROM THE COTSWOLDS, CAN ISOLATE. LARGE GARDEN
9.6 out of 10, Exceptional, (19)
"Lovely place to stay"
WORK FROM THE COTSWOLDS, CAN ISOLATE. LARGE GARDEN
Property grounds
Dove Cottage beautifully restored Tudor cottage for up to 6 in 3 rooms
9.6 out of 10, Exceptional, (52)
"My family and I thoroughly enjoyed our stay at Dove Cottage. It perfectly accommodated two elderly grandparents, three kids ages 9,14 and 17 along with my wife and I for a week’s stay in the Cotswolds. We loved the updates mixed with some of the historical nuisances of the cottage. It was appropriately outfitted to allow for multiple evenings of cooking in while also being within easy walking distance of several great local Winchcombe Pubs. We utilized the wood burning stove on a few chilly...
Dove Cottage beautifully restored Tudor cottage for up to 6 in 3 rooms
Living area
Hawthorn Cottage - sleeps 8 guests in 4 bedrooms
9.6 out of 10, Exceptional, (36)
"It is rare the Experience of staying at a holiday location works out as well as expectation of a group built up by the online marketing page. I’m pleased to say that didn’t happen here, in fact the only potential issue in advance was the parking as we had 3 cars. Even this didn’t present an issue. Excellent facilities and base, one very minor issue was the need to drink Guinness from a wine glass due to the lack of a pint glass on site, as I say very minor issue."
Hawthorn Cottage - sleeps 8 guests in 4 bedrooms
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See all available properties in Cheltenham
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.

Other types of properties in Cheltenham you may be interested in

Front of property
The George
3.5 star property
8.8 out of 10, Excellent, (402)
"My second stay at The George. A boutique hotel with pleasant friendly staff. Comfortable, tastefully decorated room with easy access to parking. An easy walk to shopping areas of the Promenade and High Street, and for Montepellier Park for the Cheltenham Jazz Festival. A diverse range of restaurants compliment cuisines from around the world, situated nearby to suit every budget. "
The price is NZ$181
per night
19 May - 20 May
The George
Reception
Queens Hotel Cheltenham
4.0 star property
8.8 out of 10, Excellent, (929)
"The hotel looked very plush from the outside and the foyer and reception area was very nice. Our room was a nice but definitely looked a little tired and in need of refurbishment. We had to be very careful with the door as it needed to be pushed tightly shut Was clean and comfortable. We would definitely stay again "
The price is NZ$194
per night
2 Jun - 3 Jun
Queens Hotel Cheltenham
Indoor pool
Delta Hotels by Marriott Cheltenham Chase
4.0 star property
8.4 out of 10, Very good, (1002)
"Had a lovely stay here - large, quiet room, firm but comfy bed, lovely bathroom facilities and a very good breakfast if no allergies. Gluten free toast provided on request but no other GF alternatives available. Staff were friendly and helpful. Pool was quite a short one for length swimming, but still it was nice to have a dip! Lovely quiet area to stay in."
The price is NZ$177
per night
19 May - 20 May
Delta Hotels by Marriott Cheltenham Chase
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cheltenham holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cheltenham. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cheltenham. Seeing all the best attractions is bound to make you fall in love with Cheltenham. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cheltenham short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Cheltenham?

Yes, there are holiday rentals in Cheltenham close to Cotswold Farm Park, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the picturesque gardens in Cheltenham. Make sure you have time to check out the sightseeing tours and musical theatre during your trip.

What are some of the best holiday rentals that Cheltenham has to offer?

Oxford Studios: This holiday home rental outside Cheltenham is near the airport, and equipped with Netflix and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Other favourite homes for rent in Cheltenham are 17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water and elegant period 5 bed house close to town centre,sleeps 15.

How many holiday rentals will I find in Cheltenham?

With 214 Expedia holiday rentals, you're guaranteed to find just the right place for your Cheltenham stay.

What can I see and do in Cheltenham?

Enjoy the outdoors at Pittville Park and Imperial Gardens, or simply take in cultural attractions like Everyman Theatre and Cotswold Motoring Museum. Other places in town to visit include The Promenade and Cheltenham Town Hall.

What are holiday rentals like in Cheltenham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cheltenham. Holiday rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a small group gathering.

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