Holiday houses in Cheltenham

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Quick stats about holiday rentals in Cheltenham

  • Total holiday rentals

    Explore 1,610 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 58,810 verified reviews to help you choose

  • Family-friendly holiday rentals

    820 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 310 rentals that welcome pets

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wi-Fi availability

    1,570 of Cheltenham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cheltenham rentals

  • 4.8 Average rating

    Cheltenham stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Cheltenham's top spots, include Cheltenham Racecourse, Pittville Park, and Everyman Theatre

Top-rated holiday rentals in Cheltenham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An open-plan living area features a wooden dining table with six chairs and a cozy seating arrangement. A large sofa faces a coffee table, while plants add a touch of greenery. Natural light fills the space through large windows, enhancing the inviting atmosphere.
Home in Cheltenham
5 out of 5 average rating, 310 reviews

Charming Coach House, fab location, highly rated!

A beautifully converted 2-bedroom Coach House in the desirable Leckhampton district of Cheltenham offers stylish living with the added benefit of free on-street parking. Ideally situated near the fashionable Bath Road and just a short stroll from the lively Montpellier & Suffolk areas, guests can enjoy a vibrant atmosphere filled with bars, cafés, restaurants, and boutique shops. The interior boasts high-specification design, making it a perfect blend of comfort and elegance in a prime location.

Guest favourite
An open-plan living space features a striking loft with a glass design above a cozy seating area. A patterned sofa and a coffee table sit on a red rug. A staircase leads to the loft, while the kitchen area is visible in the background.
Condo in Cheltenham
4.94 out of 5 average rating, 179 reviews

Pittville Loft - 5* Free parking no cleaning fee

The hidden gem of hidden gems. Our beautiful apartment is nestled in a quiet private mews lane - close to all you need and want in central Cheltenham. Free Parking inc Pittville Loft is perfectly situated for couples, young families, small groups of friends and single people traveling for business or pleasure. Within easy walking distance to the festival sites and the racecourse. Quirky and unique, Pittville Loft combines all modern conveniences with stylish vintage style and industrial chic.

Top Guest favourite
An outdoor seating area features a large table surrounded by woven chairs. A bottle of red wine and glasses sit beside a plate of snacks, including cookies and fruit. Lush greenery surrounds the patio, providing privacy, while wall lanterns add a touch of elegance.
Home in Cheltenham
5 out of 5 average rating, 48 reviews

Regency Coach House Cheltenham

A beautiful newly refurbished spacious 2 bed 2 Bathroom Coach House situated in the finest location of fashionable Montpelier Cheltenham. Wonderful open plan living with all the amenities you would expect. Explore Regency Cheltenham on your doorstep, with an array of restaurants, bars, chic boutiques and architectural history. Alternatively, visit the wonderful Cotswolds villages, just a short drive away. With free secure off road parking, this home is a perfect base for JAZZ/LIT festivals.

Top Guest favourite
A spacious studio layout features a comfortable double bed next to a cozy sectional sofa. Soft lighting from a table lamp and large window brightens the room, while a kitchenette with modern amenities is visible in the background. A striped rug adds texture to the wooden floor.
Loft in Shurdington
4.98 out of 5 average rating, 121 reviews

Modern Studio Apt close to village pub & bus stop

A modern and deceptively spacious studio apartment with its own entrance less than 2 minute walk from a lively village pub, and a 2 minute walk to a main bus route into Cheltenham. All mod cons including, high speed wireless internet, 55 inch 4K TV with Freesat, PS4, underfloor heating, double bed, sofa (can be turned into another bed. Please request extra bedding if required), well appointed kitchen, with toaster, microwave and coffee machine. Bathroom with toilet, sink and electric shower.

Guest favourite
A cozy living room is presented with light-colored furnishings. A plush sofa complements the wooden coffee table, while a flat-screen TV sits to one side. The room is illuminated by natural light from the window, adorned with soft drapes, and features a decorative fireplace.
Condo in Cheltenham
4.95 out of 5 average rating, 390 reviews

MontpellierCourtyard Apt,parking for 1 car.Sleeps4

Our courtyard apartment is set right in the heart of beautiful Regency Montpellier. Home to countless restaurants, bars and boutiques, there is something for everyone. Located directly behind the vibrant Suffolk Parade, with its eclectic mix of Independent shops, galleries and bars. It 's a 2 minute walk to Montpellier Gardens, home of some of the Festivals that Cheltenham is renowned for. Imminently approaching is The Food & Drink Festival, followed by The Jazz Festival in early July.

Superhost
A cozy living area features a deep red sofa adorned with patterned cushions, positioned against light grey walls. A reflective mirror hangs above a traditional fireplace. A soft area rug covers the floor, complemented by a warm table lamp casting a gentle glow.
Condo in Cheltenham
4.88 out of 5 average rating, 140 reviews

Stylish, town centre apartment with free parking

Fantastic location for a city centre stay. Beautiful, regency apartment, with original Georgian features, spacious rooms and luxury interior. Town centre location, 5 minute walk to John Lewis. Also walking distance to Cheltenham Racecourse. The apartment is fully equipped with Wi-Fi, fully heated and powerful water pressure! There are two bedrooms, a fully equipped kitchen, one bathroom, one luxury en-suite, This is a perfect base from which to explore Cheltenham and the Cotswolds.

Guest favourite
A well-maintained building is seen from the street, featuring large windows and a welcoming entrance. Leafy trees line the sidewalk, providing greenery. The sunny sky adds brightness to the scene, while people can be seen enjoying the outdoor space nearby.
Apartment in Cheltenham
4.92 out of 5 average rating, 244 reviews

Luxury spacious Two Bedroom Apartment, Montpellier

A luxurious spacious apartment is on the main street of Montpellier. It is quiet, being away from main roads, but in just a few steps downstairs you are on the lovely shopping street with galleries, cafes, restaurants and bars. A short stroll to the parks and shops in the centre of Cheltenham it is an ideal place to explore this lovely Cotswold town. The apartment is beautifully fitted with 2 bedrooms and 2 bathrooms. There is an allocated parking space at the back of the apartment

Guest favourite
A well-appointed bedroom features a king-size bed with a neutral-toned blanket adorned with geometric patterns. A wooden dresser and bedside table provide storage, while a circular mirror above the dresser enhances the sense of space. Soft lamps illuminate the room, creating a relaxed ambiance.
Tiny home in Cheltenham
4.96 out of 5 average rating, 193 reviews

Studio 77 Cheltenham

You will be very welcome to stay in our brand new and beautifully renovated compact and bijou tiny home which is in an easy walk of Cheltenham Town Centre and the Racecourse. We have created a gorgeous space to the rear of our family home that is completely self contained with its own entrance. Studio 77 comprises of a king size bed, kitchenette area, small seating arrangement and a good sized shower room. There is a small private patio area for guests to enjoy on a sunny evening.

Top Guest favourite
A seating area is furnished with a dark grey sofa and wooden coffee table, positioned on a patterned rug. Four dining chairs surround a wooden dining table. Light streams through two windows, complemented by burgundy curtains. A wall-mounted television is installed above the decorative media unit.
Apartment in Cheltenham
4.96 out of 5 average rating, 268 reviews

Montrose Lodge Regency Apartment, free parking(x2)

A beautifully refurbished Regency-style apartment in a superb central location. With permit street parking included for 2 vehicles within zone 1, extended parking times are available on request. The accommodation has been renovated to a high standard, featuring high ceilings, elegant period detailing, and a spacious, light-filled interior. Just a short walk to Montpellier and the Imperial Gardens, the perfect base to explore wonderful Cheltenham and all it has to offer.

Guest favourite
A comfortable bedroom is highlighted by a spacious bed with a light-grey headboard. Decorative pillows add texture. Two bedside lamps provide soft illumination. Artwork featuring a tree and Cheltenham-themed prints adorn the walls, contributing to a cozy and inviting ambiance.
Condo in Cheltenham
4.91 out of 5 average rating, 254 reviews

Stylish apartment in the heart of Cheltenham

A chic stylish one bedroom apartment in a Victorian townhouse in the centre of Cheltenham with FREE PARKING. Perfectly located to experience all Cheltenham has to offer. A short walking distance to festival locations and the most popular bars and restaurants in Montpellier, The Suffolks, Bath Road and the Promenade. The racecourse is a 25 minute walk or 10 minutes by road. An ideal base for those travelling for business or pleasure.

Guest favourite
A bright sleeping area features a spacious bed dressed in white linens, accented by decorative pillows. A nightstand with a lamp is positioned beside the bed. Large windows allow natural light to stream in, with sheer curtains partially obscuring the view.
Condo in Cheltenham
4.94 out of 5 average rating, 145 reviews

Entire quiet flat town centre - Free parking

First floor refurbished flat accessible with lift, ideally situated a few steps away from the High Street and all commodities pubs restaurants shops. Very quiet flat days and nights (facing backyard). Modern and stylish kitchen with dining area. Sleeping arrangements: -Double bed with built-in wardrobes. -Living room with best quality convertible sofa. Free Wifi, large TV in the living room and bedroom with Netflix & Prime.

Top Guest favourite
The exterior of Wycke Cottage features charming stone walls adorned with lush green vines. Multiple windows allow natural light to fill the space, while potted plants in various sizes enhance the entrance. A clear blue sky creates a serene backdrop.
Home in Painswick
4.98 out of 5 average rating, 236 reviews

Cottage luxe in The Cotwolds

Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Popular amenities for Cheltenham holiday rentals

When is the best time to visit Cheltenham?

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Avg. price$267 NZD$267 NZD$378 NZD$244 NZD$257 NZD$271 NZD$274 NZD$274 NZD$265 NZD$265 NZD$265 NZD$281 NZD
Avg. temp5°C5°C7°C9°C12°C15°C18°C17°C15°C11°C7°C5°C

Frequently Asked Questions

  • What are the best places to stay in Cheltenham?

    Explore neighbourhoods like Montpellier, which has elegant Regency architecture, or The Suffolks, known for independent shops and cafes. Around Pittville Park also draws visitors for its green spaces and leafy atmosphere.

  • What are the best things to do in Cheltenham with kids?

    Families often explore Pittville Park for its playgrounds and boating lake, visit the Wilson Art Gallery and Museum, or enjoy hands-on science at a discovery or activity centre. In summer, local lidos and splash pads frequently attract younger visitors.

  • What are some of the best things to do in Cheltenham?

    Discover Regency-era buildings along the Promenade, stroll Montpellier Gardens, or explore local markets. Art lovers visit The Wilson Art Gallery and Museum, while the restored Pittville Pump Room highlights spa town heritage.

  • How is the weather in Cheltenham?

    Cheltenham has cool winters, with January temperatures around 35–46°F (2–8°C), and mild, pleasantly warm summers reaching 55–73°F (13–23°C) in July. Rain occurs year-round, so a light raincoat or umbrella is often suggested.

  • When is the best time to visit Cheltenham?

    Late spring through early autumn is often recommended, when gardens bloom and outdoor festivals contribute vibrant energy. Cooler months bring quieter streets and a relaxed pace for enjoying local cafés and indoor sites.

  • What are the best places to visit in Cheltenham?

    Stroll the tree-lined Promenade, step inside the Pittville Pump Room, or enjoy Montpellier Gardens. The Wilson Art Gallery and Museum has changing exhibitions and local history collections.

  • What are some hiking trails in Cheltenham?

    Ascend Cleeve Hill for panoramic views, or wander gentle paths across Leckhampton Hill with its distinctive geology. Parks like Pittville Park have accessible walking routes suitable for all ages.

  • What are some family activities we can do in Cheltenham?

    Enjoy boating or picnicking in Pittville Park, explore art and history together at The Wilson Art Gallery and Museum, or splash in an open-air lido during warmer days. Local theatres sometimes host children’s performances and activities.

  • What are some of the best day trip ideas from Cheltenham?

    Explore historic Cotswold villages, walk castle ruins, or visit gardens renowned for their English floral displays around the region. The area also has country parks and nature reserves for those looking to connect with local landscapes.

  • Are there any pet friendly accommodations available in Cheltenham?

    Many Cheltenham rentals welcome pets, especially in areas near Pittville Park, The Suffolks, and Charlton Kings. Green spaces and walking trails make it easy to explore the outdoors with your companion.

  • What are some local tips for visiting Cheltenham?

    Street markets pop up regularly for fresh produce and crafts—bring a reusable bag. Locals enjoy independent cafés in Montpellier, and walking shoes are useful for exploring gardens and hilly countryside nearby.

  • What is Cheltenham known for?

    Cheltenham is well known for its Regency architecture, cultural festivals, and heritage as a spa town. Visitors often explore its lush gardens, independent shops, and vibrant arts scene.

  • What are the best hidden gems to explore in Cheltenham?

    Discover winding lanes in The Suffolks, find local art studios tucked amid the Montpellier quarter, or relax in Sandford Park with its art deco lido. Independent bookstores and markets often give a glimpse into the town’s creative spirit.

  • What are the best foods to try in Cheltenham?

    Cheltenham has locally sourced cheeses, Gloucestershire pies, and Sunday roasts commonly featured in traditional pubs. Bakeries and markets showcase scones, pastries, and artisanal cakes reflecting English and regional flavours.

  • What should I bring for a trip to Cheltenham?

    A versatile wardrobe works well—include layers for mild or cool weather, sturdy shoes for garden strolls, and a raincoat. A reusable bag is helpful for market days and local shops.

  • What is the nightlife in Cheltenham like?

    Cheltenham’s nightlife has independent bars, lively pubs, and occasional jazz or comedy venues, especially around Montpellier and the Brewery Quarter. Some venues feature local music or seasonal pop-up events.

  • What are the most popular events or festivals in Cheltenham?

    Cheltenham hosts several widely celebrated festivals, including Cheltenham Literature Festival in autumn, Cheltenham Jazz Festival in late spring, and the Cheltenham Festival, a major horse racing event. Science and music festivals also draw visitors yearly.

  • Are there family friendly vacation rentals in Cheltenham?

    Cheltenham has a range of family-friendly rentals, with many located near parks like Pittville Park or in residential neighbourhoods such as The Suffolks and Charlton Kings. These areas often have easy access to playgrounds and shops.

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