Vacation rentals in Cheltenham

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Quick stats about vacation rentals in Cheltenham

  • Total vacation rentals

    Explore 1,630 vacation rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham vacation rentals start at G$2,088 GYD per night before taxes and fees

  • Verified guest reviews

    Over 60,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    790 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 300 rentals that welcome pets

  • Rentals with dedicated workspaces

    550 properties have a dedicated workspace

  • Wi-Fi availability

    1,580 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

Top-rated vacation rentals in Cheltenham

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

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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 Cheltenham
4.98 out of 5 average rating, 232 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.

Top guest favorite
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
5.0 out of 5 average rating, 317 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.

Superhost
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
4.93 out of 5 average rating, 186 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 favorite
The living room features a prominent chandelier and an original fireplace, accented by a large mirror above it. A cozy leather sofa and a patterned rug complement the space, which includes a large dining table set for six. Tall windows with original shutters allow natural light to fill the room.
Apartment in Cheltenham
4.93 out of 5 average rating, 100 reviews

21A Montpellier Terrace: Location and Luxury

21A, the upper maisonette at 21 Montpellier Terrace has been described by guests as the perfect location in Cheltenham. Barely 100 yards from The IVY and Montpellier restaurants and across from Montpellier gardens. Built in 1835, 21A has gorgeous period features combined with a luxurious remodel. High quality furniture, bathrooms and and TV's in every bedroom. Sorry but this home is not suitable for children. Please contact me before booking if you would like to book with children.

Guest favorite
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, 412 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 favorite
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
4.98 out of 5 average rating, 120 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 favorite
A large, pale yellow building is featured with a grand entrance and multiple windows. A flowering tree with pink blossoms is visible in the foreground, surrounded by a gravel pathway and well-maintained greenery, enhancing the inviting exterior of the property.
Condo in Cheltenham
4.94 out of 5 average rating, 174 reviews

Cosy Cheltenham Hideaway

We love to welcome guests to our home and offer a large self-contained Lower Ground Floor 1 bed apartment, with its own front door, allowing guests to come and go as they please. The property has a kitchen dinner, with microwave for convenience. A large sitting room with 42” TV. There is also a log burner which guests are welcome to use. The bedroom has a new Hypnos mattress. Finally there is bathroom with walkin shower. There is also secure off-street parking on the drive

Top guest favorite
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, 282 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 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 Cheltenham
4.91 out of 5 average rating, 258 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.

Top guest favorite
A cozy living room is presented with a comfortable sofa, decorative cushions, and a flat-screen TV. Natural light fills the space through large glass doors leading to a private outdoor area with a small table and seating, surrounded by a fenced garden.
Home in Cheltenham
5.0 out of 5 average rating, 113 reviews

The Nook, Cheltenham, Town Centre-Parking & Garden

Enjoy a stylish stay at this centrally located 📍 2-bedroom coach house with chic interiors, a private garden 🌳, and free parking 🚗. Just minutes from Cheltenham town centre, you'll be steps from shops, cafes, bars 🍻, restaurants 🍔, and grocery stores. A short walk to Cheltenham Racecourse 🏇 makes it perfect for racegoers, while its 5-minute proximity to Cheltenham General Hospital 🏥is ideal for key workers. ⭐️⭐️⭐️⭐️⭐️

Top guest favorite
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, 261 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.

Top guest favorite
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.
Apartment in Cheltenham
4.97 out of 5 average rating, 242 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.

Popular amenities for Cheltenham vacation rentals

When is the best time to visit Cheltenham?

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Avg. priceG$31,736 GYDG$31,736 GYDG$44,890 GYDG$32,989 GYDG$34,242 GYDG$33,616 GYDG$32,572 GYDG$32,572 GYDG$31,528 GYDG$31,528 GYDG$31,528 GYDG$33,407 GYD
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.