Explore Cheltenham and the Cotswolds from the very best cottages in Cheltenham, including couples’ getaways, luxury cottages and dog-friendly holiday rentals.
Cheltenham is a city characterised by Regency architecture, horse racing, fine art and mineral springs, but that’s just the beginning.
When you bed down at one of the spectacular holiday rentals in the former spa town, part of the excitement is coming up with your own interpretation. The Gloucestershire town is surrounded by the Cotswolds Hills, an Area of Outstanding Natural Beauty, so country walks and day trips to stately homes also add extra scenery and excitement to any itinerary in Cheltenham.
Whether you stay at one of the holiday rentals in the town centre or a holiday home in the surrounding countryside, Cheltenham holiday cottages are well-situated for guests to visit independent shops, Cheltenham Racecourse or an art gallery, as well as to take part in watersports on the River Severn and outdoor activities in the Cotswolds AONB. If that isn’t tempting enough already, the town is also a short drive away from popular destinations in the south west, including Bath, Gloucester and Bristol city centre. Cottages in Cheltenham are some of the cosiest and most conveniently-located holiday cottages in the UK. When you arrive back home from your chosen accommodation in Cheltenham, you may very well decide that it won’t be your final visit to the Gloucestershire spa town.
8 Cheltenham Holiday Cottages for Your Next Trip:
1. 14 Northfield Passage (Cheltenham, Gloucestershire)
2. Jackdaw’s Roost (Cheltenham, Gloucestershire)
3. Wellinghill Lodge (Cheltenham, Gloucestershire)
4. Teasel Cottage (Winchcombe, Gloucestershire)
5. 3 Lake Cottages (Prestbury, Gloucestershire)
6. Belvedere Retreat (Bristol, North Somerset)
7. Self Contained Annex (Winchcombe, Gloucestershire)
8. The Pool House (Deerhurst Walton, Gloucestershire)
14 Northfield Passage
Location: Cheltenham, Gloucestershire
Best for: A cosy four-person cottage next to Cheltenham’s Brewery Quarter
Located on Northfield Passage, an alley just a few moments away from Cheltenham’s lively town centre, 14 Northfield Passage is right in the thick of the action. As Cheltenham cottages go, the holiday home is particularly cosy and modern. Warm, homely décor will settle guests in right away, as will the outdoor courtyard, where there’s a small wooden table set surrounded by plant pots bursting with greenery and a spacious barbecue. It’s an ideal space for a family of four or a couple, given that the cottage is compact and equipped with two double bedrooms, a ground-floor living room and a small kitchen-diner.
Centrally located in Cheltenham, one of the best parts about staying at 14 Northfield Passage is that you will be based within walking distance of many of the town’s sought-after attractions, including Cheltenham Town Hall and The Everyman Theatre. The cottage is located next to the Brewery Quarter, a delightful district which has everything from escape rooms to an IMAX cinema. Elsewhere in the town, there are Georgian districts to stroll around, race days at the Cheltenham Racecourse and access to footpaths into the Cotswolds AONB.
Facilities: As soon as you wake up in the morning, stick some sausages onto the grill in the electric oven and pour a glass of cold juice for the kids from the fridge-freezer. With a highchair available upon request, any families with young children are well-catered to at 14 Northfield Passage. A Smart TV will provide simple and ample morning entertainment, although you may want to waste no time in settling into the courtyard garden area for breakfast too. Other cosy features around the property add to the homely ambience, including an electric fire in the living room and a bath in the bathroom.
Jackdaw’s Roost
Location: Cheltenham, Gloucestershire
Best for: A quirky pet-friendly stone cottage with a 14-acre garden
When it comes to Cheltenham accommodation with character, Jackdaw’s Roost is at the top of its game. The stone cottage is so quintessential that it could have been plucked from the pages of an Enid Blyton or Roald Dahl novel. Set across one single ground floor, there are extensive exposed beams overhead, boho rugs and sofas in the way of decoration, an authentic woodburning stove and a ladder up to a snug mezzanine level. The quirky retreat is sure to go down a treat with those who like homes with character, and two people and one pet are handily accommodated, so no canines need to be left behind.
While the characterful holiday home is alluring enough on its own, the location is sure to please guests too. Jackdaw’s Roost is located in The Leigh, a pretty village located a short drive away from Cheltenham and Gloucester. Circled by the countryside, there are plenty of opportunities to pull on your hiking boots and get out onto country trails, perhaps accompanied by a picnic rustled up in the farmhouse-style kitchen. Combe Hill Nature Reserve is also within walking distance of the holiday home and presents an easy option for quick, scenic dog walks beside a lake.
Facilities: Quirky furniture, a woodburning stove and a cosy mezzanine level come together to form a cosy but quintessential pet-friendly getaway at Jackdaw’s Roost. This is the type of place you’ll want to snap a picture of and send to your friends for boasting rights. Even the bathroom is quirky. The décor in the bathroom includes colourful, abstract tiling and a rustic, blue-painted bathtub. The 14-acre private garden fits in well with the old-world atmosphere too; there’s a peaceful pond with reeds and lilies, a few ducks, a green paddock and off-road parking spaces.
Wellinghill Lodge
Location: Cheltenham, Gloucestershire
Best for: A log cabin on the outskirts of Cheltenham and the Cotswolds
What could be more relaxing than a secluded log cabin on a working farm on the outskirts of Cheltenham? Wellinghill Lodge is located on the outskirts of the Cotswolds, meaning that it’s just as convenient of a base for city adventures as it is for country walks and browsing idyllic market towns nestled between green slopes. Based across one ground floor rather than several, the lodge has a surprisingly modern interior including a bright and airy kitchen and a dining room. Unwind in the garden, which has a raised wooden patio with views over the green Cotswolds hills, reminiscing on the day’s adventures over a glass of wine or a tapas-style spread, perhaps.
With just a 10-minute drive, you can conquer the hike up Cleeve Hill Common or tick off the many attractions in Cheltenham, including Cheltenham Town Hall, the Montpellier Gardens and Pittville Park. The cottage is a short drive away from popular destinations in the Cotswolds AONB, including Chedworth Roman Villa, Sudeley Castle and Cerney House Gardens. With so many day trip options available from this cosy Cheltenham accommodation, you may want to end the evening with a well-deserved meal in the local pub, which is a 20-minute walk away in the village of Charlton Kings.
Facilities: Suitable for two people and one well-behaved pet, Wellinghill Lodge is a standout among Cheltenham holiday cottages for couples with a faithful furry companion. The holiday home is located in the grounds of the owners’ farmhouse, and it offers a spacious open-plan living space with a woodburning stove and well-equipped kitchen. In the adjoining room, there’s a double bed with an ensuite. Retire there after an evening unwinding on the raised courtyard area outside.
Teasel Cottage
Location: Winchcombe, Gloucestershire
Best for: A pet-friendly, 19th-century cottage in the North Cotswolds
Recharging your batteries should be easy at Teasel Cottage in Winchcombe. The three-bedroom holiday home is situated in a north Cotswolds town just 20 minutes’ drive away from Cheltenham. Within walking distance of pretty pubs, shops and Sudeley Castle, there’s plenty to do in the immediate area around Teasel Cottage. Cotswolds footpaths are always a short drive away, such as the 102-mile Cotswold Way. It’s also the perfect location for dog owners, as the property permits pets.
Hailing from the 19th century, the stone cottage might inspire guests to invent a historical itinerary for their Cheltenham getaway. Begin with a visit to Stow-on-the-Wold, the highest town in the Cotswolds. Based on the Fosse Way walking path, which follows a Roman road built in the first and second centuries, Stow-on-the-Wold is an attractive spot for hikers and budding historians. The Gloucestershire Warwickshire Railway has a station in Winchcombe, the local town, so steam train rides through the sloping Cotswolds country might also entertain guests at this particular accommodation in Cheltenham.
Facilities: The designated chef has plenty of options as to where to channel their creativity. The first option is the kitchen, which is spacious and equipped with a wooden dining table. If you’d rather eat alfresco-style, the garden has a gas barbecue and there’s a parasol-covered outdoor dining table at the end of the garden pathway. Since the holiday home is pet friendly, the whole family can be complete. Spread out, and make yourselves at home across the three cosy bedrooms and two bathrooms.
3 Lake Cottages
Location: Prestbury, Gloucestershire
Best for: A simple, two-person stay with easy access to The Wolds Way
Readying yourself for a romantic retreat in Cheltenham? You can put a hold on your search for couple-friendly cottages in Cheltenham now that you’ve stumbled upon 3 Lake Cottages. Sweet and simple, the holiday home doesn’t have any fancy luxuries like hot tubs or swimming pools, but who needs such things when there’s a small, cosy back garden with a summerhouse and seating, a traditional living room with exposed beams and easy access to the romantic restaurants in the town?
Located on the northern outskirts of Cheltenham, couples who are planning to spend a good chunk of their trip hiking should find 3 Lake Cottages particularly convenient. The Gloucestershire holiday home is surrounded by countryside and within walking distance of the Cotswold Way, a footpath which traces a 102-mile route through the countryside between Bath and Chipping Camden. Whether you base yourself at 3 Lake Cottages for a rambling break or a city break, it should be perfectly cosy.
Facilities: From the moment you swing open the front door, which is adorned with stained glass, you might be impressed by the blend between the modern and the old in 3 Lakes Cottages. Exposed beams stretch across a living room which is equipped with an electric fireplace, a leather sofa, Smart TV and a DVD player. There’s a small dining table tucked into the corner, which is one of several options for digging into steak dinners or freshly-baked banana bread. The garden also has a summerhouse and outdoor seating ideally placed for watching the sunset over the Gloucestershire countryside.
Belvedere Retreat
Location: Bristol, North Somerset
Best for: An eco-friendly lodge in a private woodland
Whether you’re a green-fingered traveller looking for an eco-friendly retreat or a family wanting a dog-friendly getaway with a hot tub, Belvedere Retreat should please. Surrounded by just over one and a half acres of private woodland, the holiday home is one of the most luxurious holiday cottages within driving distance of Cheltenham. Located in North Somerset, the retreat is under an hour’s drive from Cheltenham and under half an hour’s drive from Weston-super-Mare, Bristol and the Mendip Hills Area of Outstanding Natural Beauty.
With seaside towns and cultural cities so easily accessible from the holiday home, it might be surprising that Belvedere Retreat has such a scenic, secluded setting. The eco-lodge has a wrap-around decking with views of the trees, and there’s an electric hot tub set at the back of the holiday home surrounded by yet more greenery. Guests should have no trouble locating a local trial for birdwatching or quality time.
Facilities: As well as having a luxurious eco-lodge layout, an electric hot tub and a wrap-around decking, Belvedere Retreat has been designed to be thoroughly family-friendly. There’s a games room to entertain any young kids and a cinema room with a smart TV, sofas and a surround-sound system should they need another place to unwind. Adults can gather around the ground-floor bar, which has a dart board, disco lighting and a vinyl player. Also based on the ground floor, there’s a dedicated dog shower to wash off any muddy paws and a sauna room for those in need of extra relaxation.
Self Contained Annex
Location: Winchcombe, Gloucestershire
Best for: A couples’ retreat on the Cotswold Way walking trail
With views of miles of pristine Gloucestershire countryside, the two-bedroom Self Contained Annex is well-suited to a couples’ getaway. Almost directly on the Cotswold Way walking path, dates in the daytime might involve hiking through green slopes and market towns or dining in local gastro pubs. Come night-time, light a firepit on the patio and witness the sunset over the farm fields which stretch out before the property. There’s none of the additional noise that often comes with very central cottages in Cheltenham, unless you count the neighing of sheep in the surrounding fields.
Despite its rural location, The Paddocks Self Contained Annex is still only a short drive from the town and sites like Cheltenham Town Hall and the Grade II-listed Everyman Theatre. As a market town, Winchcombe has a large selection of delightful eateries, pubs and a market, all within walking distance of the holiday home.
Facilities: After parking in the two off-road parking spaces, access to the Self Contained Annex can be found through a small, wooden gate and a tall hedge. The holiday home is a compact and cosy place with an open-plan living space consisting of a kitchen, dining area and a living room warmed by an electric fire. The most spacious area is the courtyard, which looks over the owners’ family farm and has a firepit, a dining table and a parasol.
The Pool House
Location: Deerhurst Walton, Gloucestershire
Best for: A luxury two-bed getaway with swimming pool access between Cheltenham and the Malvern Hills
Looking for luxury accommodation in Cheltenham and the surrounding area? The Pool House is a one-bedroom retreat which fits the bill. The single-storey, barn-style holiday home has a large range of luxury amenities, from an open firepit and gazebo in the glorious back garden to access to a communal indoor swimming pool, hot tub, sauna and gym. Other mod cons in the cottage include a 42-inch TV with Netflix, Amazon Prime Video and WiFi. With crawlers and plant pots draped over the holiday home and extensive gardens as well as a central courtyard with rattan furniture rolling out on all sides, this is an excellent place to unwind as a couple.
When you’re ready to tear yourself away from the pool and sauna, The Pool House is under half an hour’s drive from Cheltenham and the Cotswolds AONB. There’s a shop half a mile away for couples who are looking forward to romantic dinners or barbecues in the back garden. Alternatively, take the walk to the pub that’s under two miles from the property, and let someone else take care of the cooking one evening. More green slopes can be tracked down in the Malvern Hills Area of Outstanding Natural Beauty, which is under half an hour’s drive to the northwest of The Pool House.
Facilities: With a range cooker, gas hob, electric oven, microwave and fridge at your disposal, The Pool House has a convenient assortment of cooking equipment for couples who like to spend their quality time cooking. Get cosy in the garden on summer evenings, as the patio is equipped with a barbecue. There’s a further set of furniture, a hammock, a gazebo and a firepit in the garden. The open-plan living area has a cluster of books and board games available should you want to entertain yourselves the traditional way.
Book the Best Holiday Rentals with Breakfree Holidays
Whether you’re heading to Cheltenham to base yourself near the Cotswolds’ many extraordinary hiking trails or to have a town break full of good food, sightseeing and other simple pleasantries, these holiday homes will get your break off to a great start. If you’re still undecided about where to visit, we at Breakfree Holidays have a large offering of holiday cottages in the UK. Why not check out the cottages in Somerset and the Cotswolds or holiday cottages in Wales, two nearby destinations? Start dreaming, and book your next trip today.