Holiday rentals in Cheltenham

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Top-rated holiday rentals in Cheltenham

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A modern kitchen space features sleek white cabinets and an integrated oven. A wooden countertop provides an inviting area for meal preparation, while stainless steel appliances complement the clean design. Natural light enters through a nearby window, enhancing the bright and functional atmosphere.
Apartment in Henleaze
4.87 out of 5 average rating, 366 reviews

Modern studio in the heart of Cheltenham

Enjoy your stay in this centrally located studio apartment on the top ( second ) floor. Ideally located for all the wonderful bars cafes and restaurants that Cheltenham has to offer, this easy living, modern studio apartment is on the doorstep to all the activity. You will see instructions for entry 48 hours before arrival. GL52 2SQ There is a secure side door for bike storage on ground floor. Cheltenham Racecourse is a 5 minute drive ( traffic dependent ) or a 30 minute walk from apartment.

Guest favourite
A self-contained studio flat features a spacious bed with colorful bedding and freshly folded towels placed on top. A cozy sofa complements the room, with a large window allowing natural light to fill the space. A small alcove with a mirror is positioned nearby.
Flat in Henleaze
4.85 out of 5 average rating, 120 reviews

New Town Centre Studio Flat

Whatever you’re in Cheltenham for, this newly renovated self-contained studio flat is the perfect location for your stay. 5 minutes walk from the high street and from the fantastic bars and restaurants of Montpellier. Round the corner from the hospital and with the beautiful Sandford Park Gardens and Lido on the doorstep. The studio is the ideal bolthole with permit parking available, key pad entry, kitchen area, newly fitted bathroom, bedroom area and sofa (sofa bed for an additional fee).

Top guest favourite
The living area features a cozy seating arrangement with a neutral-toned sofa and decorative cushions. A natural woven pendant light hangs above, illuminating the space. A rustic coffee table sits on textured flooring, accompanied by warm tones and a charming wreath adorning the entrance.
Cottage in Winchcombe
4.98 out of 5 average rating, 211 reviews

Little Nook Cottage - Dog Friendly & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Guest favourite
A colorful armchair with patchwork fabric is positioned beside a slender lamp, creating a cozy reading nook. A tall window allows natural light to illuminate the space, complemented by light sheer curtains. A small side table and decorative elements add charm to the inviting room.
Flat in Henleaze
4.88 out of 5 average rating, 197 reviews

Stunning Regency flat with parking town centre

This Beautiful Regency 1 bed apartment with 1 parking spot (available from 4pm check in to 12 noon check out please) is suitable for adults only. House is situated within walking distance of Cheltenham racecourse, all shops, parks, restaurants and theatres. It has been recently been refurbished . Lovely new carpets and furniture throughout…. Sitting room, kitchen are on one floor with a fabulous double bedroom and a lovely luxury bathroom with shower and large bath tub on the top floor.

Top guest favourite
The entrance to the Garden House is framed by a sturdy tree and vibrant potted plants, showcasing colorful flowers. A wooden table and shelf stand beside the door, enhancing the welcoming appearance of this independent annex.
Tiny home in Gloucestershire
4.93 out of 5 average rating, 754 reviews

The Garden House in Kingsholm, Gloucester

The Garden House is a lovely single room annex with independent access, en-suite bathroom and shower. Light, cosy, and simply furnished, set in the garden of a residential home near the centre of Gloucester, it's a quiet space to relax or work. Driveway parking available. A two-minute walk to the famous Kingsholm rugby stadium and food shops, ten minutes to city centre, bus and train stations, cathedral, Quays shopping outlet, restaurants and historic docks. Easy bus route to Cheltenham.

Top guest favourite
A spacious sitting area features a light-colored sofa and a wooden coffee table on a patterned rug. Glass doors open to a private patio with outdoor seating, surrounded by greenery. An original marble fireplace adds character to the room, and a television is positioned beside a wooden media unit.
Flat in Henleaze
5 out of 5 average rating, 134 reviews

Rosebank - Spacious apartment in Montpellier.

Welcome to Rosebank, a self-contained basement apartment with a spacious, homely and creative vibe. The bedroom has a king size sleigh bed. There is a private entrance at the front and access at the back to your own south facing courtyard. Where possible a free guest parking permit can be arranged. Montpellier is a vibrant and chic area with excellent restaurants, bars & boutique shops. Easy access to the outstanding cotswold countryside makes it the perfect location for holidays or work.

Top 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.
Apartment in Henleaze
4.96 out of 5 average rating, 359 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.

Top guest favourite
The kitchen area features a light marble countertop with a sink, complemented by modern pendant lighting. In the background, a cozy living room is visible, furnished with a dark sofa and colorful cushions, highlighted by natural light from large windows.
Flat in Henleaze
4.93 out of 5 average rating, 330 reviews

The Best address in Montpellier, Cheltenham

This wonderfully spacious apartment is situated in the heart of fashionable Montpellier where you will find an incredible array of Independent shops and prestigious eateries such as The Ivy ,Giggling Squid , The Daffodil and the renowned Michelin starred Le Champignons Savage,a new find is Kibousushi located about 200 metres from the apartment ,a new find for us and an amazing Japanese restaurant ,but you have to book in advance . The home of horse racing is just a 20 minute walk .

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.
Flat in Henleaze
4.97 out of 5 average rating, 235 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 spacious room features a comfortable king-size bed covered with a textured yellow quilt. A kitchenette is visible in the background, alongside a wooden table. Natural light enters from a nearby window, illuminating the simple decor, which includes a dresser and casual seating.
Guest suite in Henleaze
4.88 out of 5 average rating, 372 reviews

The Garden retreat

The Garden room has its own front and back door, and access to a lovely south facing garden. It has a kitchenette and en suite. It has a very comfortable king-size bed. We are 10-15 minutes walk from the town centre and have views onto Cleeve Hill the highest point of the Cotwolds. There are good local pubs, a national award winning fish and chip shop and a supermarket all nearby. Perfectly situated for all Cheltenham festivals.

Guest favourite
A spacious bedroom features a king-sized bed with white linens and decorative pillows. Natural light enters through multiple windows, illuminating the room. A comfortable chair and side table are positioned nearby, adding to the cozy ambiance. Soft colors complement the serene atmosphere.
Flat in Henleaze
4.86 out of 5 average rating, 348 reviews

Private flat, close to town centre with parking

A large well appointed and spacious double bedroom, with ensuite bathroom, fully equipped kitchen diner and private entrance. This apartment is totally self contained with off road private parking and is only a 15-20 minute walk into the town centre. A fantastic base for exploring the Cotswolds, or just enjoying the festivals and shopping that Cheltenham has to offer.

Guest favourite
The lodge is viewed from a wooden gate, framed by trees. The structure features large glass windows, revealing a bright and open design. Rolling hills can be seen in the distance under a clear blue sky.
Guest house in Gloucestershire
4.92 out of 5 average rating, 616 reviews

Cotswold lodge with amazing views and famous walks

Enjoying spectacular views this 2 bedroom, dog friendly lodge sits on the top of Leckhampton Hill, enjoying easy access to the famous ‘Cotswold Way’ walk and is a 5 minute drive from the town centre of regency Cheltenham. The Lodge also includes a 3.5m outdoor kitchen looking over The Malvern Hills. The kitchen includes a large built in BBQ, a pizza oven and sink.

Popular amenities for Cheltenham holiday rentals

When is the best time to visit Cheltenham?

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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.

All about Cheltenham

As a well-to-do town with one foot in the countryside, Cheltenham offers the best of both worlds. This attractive urban hub, best known for its internationally acclaimed festivals and immaculate Regency architecture, fizzes with culture and fine dining, with the rural idylls of the Cotswolds close by.

Mineral springs discovered in the early 18th century built Cheltenham into an early tourist spa town in the style of Bath; it became popular in the 18th and 19th centuries, when latter-day hipsters came to sip the curative waters that bubble up here. Exquisite parks and promenades developed during that era still add to its appeal, including Pittville Park, home to a boating lake, and the magnificent Pittville Pump Room, now an events space and cafe, adorned with fluted Ionic columns and housing the original marble water pump.

In town, leafy shopping districts around the Promenade, Montpellier, and the Suffolks — a square of colourful Georgian townhouses — feature independent stores, bars, cafes, and the Wilson Art Gallery and Museum.

What are the top things to do in Cheltenham?

Holst Birthplace Museum

Go back in time to see a typical 19th-century domestic setting at this home of the famous composer. The piano on which he composed his best-known seven-movement suite is still in the music room.

Sandford Parks Lido

The bathing suits may have changed, but the nostalgic design of this 1930s lido is little altered. A 50-metre heated outdoor swimming pool backed by lawns is accompanied by a children’s pool with slides and a paddling pool. In summer it hosts outdoor movie screenings, with deckchairs for the top seats. The main summer period usually runs from May to October, but there are cold-water swimming sessions for hardcore swimmers during the winter.

Sudeley Castle

To the northeast of the city, Sudeley Castle is one of the closest Cotswolds attractions, and an absolute stunner with 10 distinct gardens bursting with flowers. A millennia of history is packed into the castle’s crenellated walls, and Katherine Parr, the last wife of King Henry VIII, is buried in the grounds.

Quick stats about holiday rentals in Cheltenham

  • Total holiday rentals

    Explore 1,600 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 55,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    750 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 300 rentals that welcome pets

  • Rentals with dedicated workspaces

    570 properties have a dedicated workspace

  • Wifi availability

    1,550 of Cheltenham holiday rentals include wifi 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

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