Family-friendly vacation rentals in Cheltenham

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Top-rated family-friendly rentals in Cheltenham

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Guest favorite

Cottage in Cheltenham

4.9 out of 5 average rating, 417 reviews

The Bothy cottage in the Cotswolds

The Bothy is a conversion of a 17th Century Cotswold stone stable and a 20th Century kennel building. On the ground floor is the living room with a beautiful wood burning stove, a fully equipped kitchen, a comfortable double bedroom and a modern shower room. Whilst upstairs, which is accessed from a narrow oak staircase, you can find the twin bedroom. The living room has been fitted to retain all its original features and is furnished in period style. I have included many Georgian and Victorian pieces and have also included a large settee and two arm chairs, dining table and chairs for 4, corner cupboard and a dash of the 21st Century with a Sky television. The Bothy is beautifully situated in the Postlip Coombe on the leeward side of the Cotswolds highest hill and yet only minutes from Winchcombe, a classic Cotswold "wool" town, renowned for its excellent shops, restaurants and architecture.

Oct 22 – 29

G$26,206 GYD per night

Guest favorite

Apartment in Gloucestershire

4.98 out of 5 average rating, 170 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.

Jun 6 – 13

G$22,183 GYD per night

Guest favorite

Apartment in Shurdington

4.95 out of 5 average rating, 352 reviews

Rivendell Annex close to Cheltenham

The Annex is a completely self contained open plan 2 double bedroomed groundfloor apartment with patio area and off road parking. The entrance has a small 7inch step - once inside bedrooms bathroom kitchen dining and lounge areas are on one level. Access to the patio via patio doors - 3 small steps, each 5inches in height and another smaller step leads to the main garden. Situated within easy access to the M5 motorway and close to local bus routes ideal for exploring pretty Cotswold villages.

Nov 30 – Dec 7

G$26,854 GYD per night

Guest favorite

Condo in Cheltenham

4.98 out of 5 average rating, 306 reviews

Footsteps from the town & parks (+ hamper/parking)

Little Portland is a central 700 sq ft self-contained Grade-II apartment moments from the heart of town & Pittville Park (a historic area, with two lakes, cafes and a kids' play area). If you're coming to visit the town, races, festivals or Cotswolds, it's ideal. Parking centrally can be tricky so we offer guests 2 free parking permits. You'll also receive a food hamper with beer or cider, nibbles, brioche, fruit, milk & juice. The apartment has a cooling system for the summer months.

Nov 2 – 9

G$23,194 GYD per night

Guest favorite

Apartment in Cheltenham

4.92 out of 5 average rating, 188 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 main shopping street with all of the 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

Jun 15 – 22

G$32,372 GYD per night

Guest favorite

Guesthouse in Gloucester

4.96 out of 5 average rating, 339 reviews

The Hut and Tub

Cosy Centrally Heated Shepherds Hut With luxury hot tub In Quiet Rural Area The perfect 'country getaway' for two people. This small shepherds hut is tucked away in the heart of a quiet Gloucestershire village situated in the corner of our garden but completely private and not overlooked with its own decking and luxury hot tub overlooking fields and farmland. The river Severn is less than a mile away which has a footpath all the way to Tewkesbury and nearby pubs.

Oct 7 – 14

G$30,049 GYD per night

Guest favorite

Place to stay in Charlton Kings

4.93 out of 5 average rating, 237 reviews

Studio Garden Room, relaxing & comfortable

Our clean and comfortable studio garden room is perfect for a break away from home. Great space for 1 or 2 guests, comfortable bed, equipped kitchen, tv and wifi. Cheltenham town centre is a pleasant walk away or easily accessible by bus or car. We have always taken pride in the level of cleanliness at each changeover and have increased our thoroughness in light of recent guidelines with regard to reducing the spread of infectious diseases.

Aug 21 – 28

G$20,984 GYD per night

Guest favorite

Guest suite in Churchdown

4.92 out of 5 average rating, 168 reviews

Apartment with bathroom and kitchen

Our flat offers twin bedded room with shower room, kitchen, Internet, TV and underfloor heating. Sunny aspect with windows on both sides. View over garden and countryside. The house is set back about 100 yards from the road and is therefore quiet. It has plenty of off road parking and a bus stop outside. Within 400 yards we have a pub, Chinese and Indian restaurants, cafe and newsagents. Nearest supermarket is one mile away.

Sep 5 – 12

G$13,474 GYD per night

Guest favorite

Apartment in Gloucestershire

4.88 out of 5 average rating, 136 reviews

Pittville apartment, walk to town and the races

A spacious (80sqm/860sqft), recently modernised and decorated garden apartment within a beautiful, Grade 2 listed Regency building overlooking Pittville Park in a quiet residential area. There are two well appointed bedrooms both with en-suite bathrooms, a well equipped and large kitchen/diner and a similarly large living room with 40” TV, DVD player and table football table. Wi-Fi is accessible throughout the apartment.

Sep 17 – 24

G$28,249 GYD per night

Guest favorite

Apartment in Cheltenham

4.88 out of 5 average rating, 240 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 parking and is only a 10-15 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.

Apr 6 – 13

G$13,974 GYD per night

Guest favorite

Barn in Gloucester

4.99 out of 5 average rating, 155 reviews

Rural retreat - Hen House, contemporary & spacious

A former chicken shed; the hen house is individual, light, and offers spacious, comfortable, well-equipped accommodation in a rural location. Ideal for exploring the area, for couples wanting to enjoy a quiet, romantic break or a great bolt hole to work or study - you can close up the shutters, lock yourself away and no-one will know you are there!

Aug 24 – 31

G$30,623 GYD per night

Guest favorite

Condo in Cheltenham

4.98 out of 5 average rating, 452 reviews

Beautiful Two Bedroom Apartment

A spacious, 1000 sq ft / 92 sqm, two double bedroom apartment, taking up the entire lower ground floor of a beautiful Grade II listed Villa in central Cheltenham. Self contained, it has its own entrance, two bedrooms, a separate kitchen, separate sitting room, and bathroom with shower. It also has super fast 150mb wifi broadband.

Oct 22 – 29

G$37,522 GYD per night