Holiday rentals in Cheltenham

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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, 292 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.

Top guest favourite
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.
Flat in Cheltenham
4.98 out of 5 average rating, 214 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.

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.
Apartment in Cheltenham
4.95 out of 5 average rating, 155 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.

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 Cheltenham
4.84 out of 5 average rating, 143 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 favourite
A modern living area features a cozy grey sofa adorned with soft pink cushions, complemented by a comfy armchair with a decorative throw. A round mirror is positioned on the wall, while framed artwork adds a touch of sophistication. Warm lighting extends across the space.
Flat in Cheltenham
4.92 out of 5 average rating, 209 reviews

Best located Flat in Cheltenham + Free Parking

Luxury, modern, 5* apartment in the heart of Montpellier, Cheltenham. Centrally located, just a minutes walk from Cheltenham’s prestigious shopping on The Promenade. Montpellier bustles with bars & restaurants including The Ivy and 131. The apartment is set back off Montpellier Street in The Courtyard so has more privacy. A huge benefit is the free of charge, private parking space. If you’re here for one of Cheltenham’s festivals Imperial Gardens and Montpellier Gardens are opposite the flat.

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.
Flat in Cheltenham
4.92 out of 5 average rating, 241 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

Top guest favourite
A spacious sitting room featuring a fireplace and a large mirror reflecting natural light. Elegant furnishings include a comfortable sofa, a coffee table, and a decorative chandelier overhead. A wooden desk and chair provide a functional workspace, complemented by gentle tones and soft textures throughout.
Home in Cheltenham
4.97 out of 5 average rating, 112 reviews

Georgian townhouse in famous Suffolks area

A unique opportunity to stay in a beautiful Grade 2 listed Georgian townhouse in the famous Suffolks area of central Cheltenham with four bedrooms and six beds. Easy walking distance to all amenities, bistros and restaurants (5 min), Montpellier, the Promenade shops and Bath Road (10 min), racecourse (40 min), Cricket festival (5 min) and Literature, Jazz, Music and Science festivals (5 min). Perfect for Race Week, and a great base for touring the Cotswolds. Free parking nearby

Top guest favourite
The entrance of a historical building showcases a bright yellow door flanked by decorative wrought iron balconies. Potted plants are positioned on either side of the entrance, complementing the stone facade. Steps lead to the front door, framed by classic wrought iron fencing.
Apartment in Cheltenham
4.95 out of 5 average rating, 161 reviews

Regency flat, private courtyard, free parking

A beautiful recently renovated Regency flat in a grade II* building. We are 5 minutes walk to the city centre and 25 minutes to the Racecourse. The flat has its own front door and private courtyard. Virgin VIP package and high speed broadband plus Sky & BT Sports. One kingsize bed with soft linen sheets, plus one sofa bed for additional guests (book for 3 if you want the sofa bed). Well equipped kitchen. Separate shower room (off living room). Free parking nearby. Nest heating.

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 Cheltenham
4.96 out of 5 average rating, 249 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
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 Cheltenham
4.95 out of 5 average rating, 151 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 favourite
A cozy living area features a gray sofa with patterned cushions, positioned beside a modern fireplace. A low coffee table holds fresh fruit, while bookshelves line the walls. Natural light enters through windows covered by blinds, enhancing the bright and inviting space.
Flat in Cheltenham
4.98 out of 5 average rating, 230 reviews

Self-contained basement flat in regency home

Refurbished basement flat in grade 2 listed regency terraced house. Central Cheltenham location, walking distance to all local festivals, shopping, pubs and restaurants. Modern, light and spacious accommodation with private access and patio terrace via the bedroom. Good size bathroom with bath and walk-in shower. There is no separate kitchen but an area containing a fridge, microwave, kettle & toaster.

Top guest favourite
The lounge area features two comfortable sofas, one adorned with bright orange cushions. A small coffee table holds a collection of magazines. A decorative fireplace serves as a focal point, and a muted art piece hangs above it, contributing to a cozy ambiance.
Serviced apartment in Cheltenham
4.97 out of 5 average rating, 100 reviews

Luxury Refurbished 2 Bedroom Regency Apartment

Superbly Appointed Regency Apartment Situated Along A Tree Lined Road Close To Cheltenham Centre Where You Will Find A Plethora Of Amazing Shops & Restaurants. With Its Own Private Entrance This Luxury Apartment Has Been Refurbished To A High Standard Throughout & Offers Spacious & Comfortable Living. It Is Suitable For Up To 4 Guests, Couples, Families Or Corporate Stays.

Popular amenities for Cheltenham holiday rentals

When is the best time to visit Cheltenham?

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Avg. price$171 SGD$165 SGD$255 SGD$178 SGD$187 SGD$197 SGD$200 SGD$200 SGD$194 SGD$194 SGD$194 SGD$205 SGD
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.

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 $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 57,620 verified reviews to help you choose

  • Family-friendly holiday rentals

    760 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 300 rentals that welcome pets

  • Rentals with dedicated workspaces

    580 properties have a dedicated workspace

  • Wifi availability

    1,570 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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