Vacation rentals in Cheltenham

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Top-rated vacation rentals in Cheltenham

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Top guest favorite
The exterior of a charming brick building is displayed, featuring a symmetrical design with large windows framed in white. A subtle front door with a circular window is central, flanked by neatly arranged planters and greenery, creating a welcoming presence.
Apartment in Henleaze
4.98 out of 5 average rating, 207 reviews

Beautiful basement flat. Leckhampton, Cheltenham

Beautiful self contained basement flat with own entrance. Open plan living area with pull down ‘Murphy bed’ (please ask when booking if you would like to use this bed as it requires host assembly). Full kitchen-dishwasher,oven,microwave & washing machine. Bedroom with wardrobe, dressing table and king size bed- can be separated into 2 singles on request at time of booking. Wet room with shower. Shampoo,conditioner,shower gel and towels provided. Tea,coffee,milk and breakfast items provided.

Superhost
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.
Condo in Henleaze
4.88 out of 5 average rating, 361 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 favorite
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.
Apartment in Henleaze
4.87 out of 5 average rating, 104 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).

Guest favorite
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.
Apartment in Henleaze
4.88 out of 5 average rating, 184 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 favorite
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.
Apartment in Henleaze
4.93 out of 5 average rating, 327 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 favorite
The exterior of the property features a charming brick facade, complemented by multiple windows that allow natural light to fill the interior. A covered entrance leads to the home, while wooden storage units provide practical outdoor space on the side.
Home in Henleaze
4.99 out of 5 average rating, 178 reviews

7 Diamond Jubilee, Cheltenham

Diamond Jubilee is a unique fully electric property located in a quiet little mews street but a short walk to the bars, shops, and restaurants of the vibrant area of The Suffolks and Montpellier. Cheltenham has a thriving cultural scene and hosts numerous festivals throughout the year such as the jazz, food and drink, literature, and science. Undoubtedly, the highlight of the year is the annual racing festival, The Gold Cup at Cheltenham Racecourse. Newly renovated bathroom.

Top guest favorite
An open-plan living and dining area is showcased, featuring a large dining table with red chairs. A patterned area rug lies on the floor, while a comfortable seating arrangement is visible in the background. Soft lighting is provided by pendant fixtures above the table.
Home in Henleaze
4.96 out of 5 average rating, 137 reviews

Charming house in the centre of town.

A centrally located charming house. Just a short walk from the trendy Montpellier area and High Street it’s perfect for a city break. The house has a spacious open plan living/dining area with separate kitchen, two spacious bedrooms, bathroom and courtyard garden. There is a comfy fold down king size Murphy bed in the living room. Included in your booking is a parking permit for one vehicle. Additional parking permit available for a small fee.

Top guest favorite
The exterior features a newly refurbished annexe with a clean, modern design. A stone pathway leads to a private entrance, surrounded by gravel and paving. A small area of artificial grass and a garden shed are visible, providing a welcoming outdoor space.
Guesthouse in Henleaze
4.92 out of 5 average rating, 370 reviews

Beautiful Self-Contained Annexe in Cheltenham

A lovely, newly refurbished annexe, perfect for 1 or 2 guests within good distance to the town center. A cosy, fully functioning, self-contained home from home featuring a double bed, kitchenette, en suite bathroom, 32" TV, heated floor and radiator with a private entrance. Located a 30 minute walk from the town centre and the Brewery Quarter, which is full of restaurants and bars, 2 cinemas, Mr Mulligans Adventure Golf and Hollywood Bowl.

Guest favorite
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 Henleaze
4.92 out of 5 average rating, 233 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 favorite
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
4.87 out of 5 average rating, 366 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 favorite
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.
Guesthouse in Gloucestershire
4.92 out of 5 average rating, 606 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.

Guest favorite
The modern kitchen features a spacious island with a wood countertop, complemented by grey cabinetry and stainless-steel appliances. Abundant natural light streams through overhead windows, illuminating the open layout. A wall-mounted TV is visible in the background, providing a focal point for the space.
Townhouse in Henleaze
4.86 out of 5 average rating, 281 reviews

Cheltenham Superb 2 Bed Townhouse, The Suffolks

Recently refurbished, Traditionally Modern Townhouse in the Suffolk’s area of Cheltenham ... an area often referred to as the Notting Hill of Cheltenham, with an eclectic mix of independent cafes, bars, restaurants and shops, all on your doorstep Virgin Media SuperFast Fibre Broadband throughout, ideal for streaming and home working purposes.

Popular amenities for Cheltenham vacation 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.

Quick stats about vacation rentals in Cheltenham

  • Total vacation rentals

    Explore 1,600 vacation rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham vacation rentals start at $10 per night before taxes and fees

  • Verified guest reviews

    Over 55,020 verified reviews to help you choose

  • Family-friendly vacation rentals

    750 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 300 rentals that welcome pets

  • Rentals with dedicated workspaces

    570 properties have a dedicated workspace

  • Wi-Fi availability

    1,550 of Cheltenham vacation 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

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