
Kid-friendly holiday rentals in Winchcombe
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Top-rated family-friendly rentals in Winchcombe
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Kid-friendly house rentals

Boddington Mill, Enchanting 3 Bdr Retreat by Oriri
Such a lovely place. Sadly, I only had a couple of nights and one day to really enjoy it, but I immediately looked to re-book upon departing, and although the dates I looked at did not work, I will definitely return. Joe was really friendly and helpful. The house is lovely, well-designed and thought through with plenty of space. The weather was a bit damp, but otherwise we would have also thoroughly enjoyed the lovely garden with its seated areas and hot tub. Many thanks for a lovely break

Iconic 17th Century Thatched Cottage
Everything was great. The place was adorable.

Bourton on the Water Scandi Chic Authentic Cottage
We loved our time in the Jasmine Cottage! After 5 busy days sight seeing in London, this was the perfect place to stay with our 8 and 5 year old sons to just relax and enjoy a slower paced few days. A 1 minute walk (at most) to the town shops, restaurant, and water. Everything looked exactly like the photos, the host was extremely responsive and helpful, and the location could not have been better. We already miss it and will look back fondly on our time at Jasmine Cottage for many years to come!

Anchor Weighbridge House Winchcombe - 4 bedroom
Superb comfortable location for a few days in the Cotswolds. The rear patio and garden was a real afternoon and evening sun trap. Had an excellent meal at The Lion only 1minute down the road. We walked to Sudeley Castle, recommend for a least 2hrs if you like a bit of history then onto Belas Knap, a 5,500year old burial site, then down the hill back to Winchcombe. Cleeve hill walk provided incredible views and Cheltenham is 20minutes away. The Jazz festival was in full swing.

Magical cottage set within a woodland glade
This is my third time visiting Badgers Bothy and we've made it 4 for next year! It is a little peace of heaven, set in the most gorgeous setting. If you are looking for a place to relax, unwind and forget about things for a few days then Joe's place is perfect for this. It's beautifully decorated, beautifully clean and feels like a second home from the second you walk through the door. The wildlife is an additional bonus - sat in the living room watching a Muntjac walk past was just the cherry on the top. Thanks Joe for another lovely visit, we are very much looking forward to coming back next year x

Stylish Cotswolds Chapel Stunning Valley Views
Stay here! If you are visiting the Cotswolds, this is a great choice. Very unique but very comfortable ‘home’. The remodel is so tasteful and functional. The surroundings are gorgeous. The pub is walkable. Jacks Green is a great village, and we visited a dozen of them. One note: the roads are very narrow…caution when driving and walking. Overall, 5-star stay! Don’t miss this one.

Deluxe Coach House at Bretforton Manor with pool
We had a great 4 nights at Lucy’s. The garden is breathtaking, the pool lovely and a short walk takes you to the historic pub (complete with Morris Dancers). Lucy was very welcoming and friendly and the house comfortable and within easy travelling distance of some of the best parts of the Cotswolds. We would love to return. Thanks Lucy!

Luxury Cottage with Heated Pool
Beautiful home! Absolutely loved staying here. The grounds were so gorgeous and the property was 5 star hotel standard. It’s not often that you stay somewhere that the beds are comfier than your own and these were. They had thought of every little detail. Couldn’t recommend more.
Family-friendly apartment rentals

Private flat, close to town centre with parking
Emily's flat is spacious, well-furnished, comfortable, with all amenities you might need and is very close to the Town Centre. Emily goes above and beyond the usual Airbnb experience by providing a selection of cereals, milk, tea, fresh coffee, juice, bread, butter and jams! Emily provided excellent check-in instructions was quite communicative. Thank you for making my trip to Cheltenham so memorable. I will be definitely looking to book your flat the next time I am in Cheltenham.

The Old Post Office, Central Broadway with Garden
We loved our stay at The Old Post Office. Elizabeth was a great host and made us feel welcome and right at home. The location in Broadway can’t be beat and we would recommend Elizabeth’s home to anyone wanting a great base to explore the Cotswolds.

Retreat for a Cotswolds Getaway
Theresa was very flexible with our arrival arrangements, which greatly helped our stay. Although we only stayed a single night the apartment is spacious and well enough equipped for a longer stay. No hesitation in recommending.

A Beautiful luxury two bedroom Hayloft
A really lovely apartment, very clean with all the little extras. I loved the balcony and view. Excellent and easy parking. It is one of the best cottages I've stayed in with my two teenagers - there's a great chill out sofa but there was enough room to have our own space if needed. I've booked again for Aug it was that nice.

Elegant regency garden flat with parking
Great hosts, great communication. Lovely, spacious, clean and well-equipped apartment with parking in a great location. The private outside seating area off the bedroom is a lovely bonus. Highly recommended. Nice restaurants and bars near Montpelier Gardens.

The Best address in Montpellier, Cheltenham
An exceptional apartment with everything you may need for a short stay in Cheltenham. Suzanne thoughtfully left a welcome basket of goodies which was a very sweet touch. Thank you for a wonderful stay.

Cotswold Garden Hideaway, by R.Avon
I was a guest at a wedding at Twyning Park and found Terry’s accommodation to be stellar and perfectly suited to my needs for my weekend stay. Terry was super accommodating of any requests and I’d highly recommend his place. Thanks again!

Self-contained basement flat in regency home
Super place to stay, great location and really comfortable. Julian was really friendly and made sure our visit was a pleasure. Highly recommend.
Family-friendly apartment rentals
Historic Renovated Apartment in Riverside town
A great place to stay to explore Upton and the surrounding areas. Apartment is great in a central location right in town, easy walk to anywhere in Upton. Carola and Rick were great hosts, good clear instructions and helpful information. Apartment was spotless (thank you to their housekeeper Emma), and would highly recommended both the Regency Apartment and Carola and Rick as hosts.

2 Double bedroom flat in the heart of cheltenham
Great little place very central in town. We were in Cheltenham for the jazz festival and the flat was excellent for walking to the venues, restaurants and shopping. Ideal for what we wanted. Comfy bed and a nice touch of bottled water provided. It was a very warm day but the curtains had been closed before arrival and a fan provided which was very welcome. Thank you for a great stay.

Modern studio in the heart of Cheltenham
Everything you could possibly need was there - even a fan, which I really appreciated! Kitchen was well stocked with implements. Bathroom as super clean - as was the whole flat. Great little room :)

Stunning 2 Bed in the Heart of Cheltenham
An exceptional Airbnb in the heart of Cheltenham. It is a beautiful and stylish home with thoughtful touches. We were met with delicious home made scones on arrival. Doug was very communicative, getting back to me almost instantly. The flat is a great size, well laid out, with incredibly comfy beds and a delightful courtyard that we enjoyed in the sunshine. Just a few minutes walk from the center of Cheltenham with on street parking. Highly recommend and can’t wait to return.

Luxury 1 bed, Broadway, Cotswolds. Private parking
We spent a weekend at Claire's and had a lovely time. The place is as described and a perfect location for a stroll into Broadway and for exploring the Cotswold's. Would highly recommend

Central Top floor Apartment /Free Zone12 Parking
Natalia’s apartment was perfect for our stay in Cheltenham. I would highly recommend it and will definitely stay again!! Thanks for being such a great host.

Stylish apartment in the heart of Cheltenham
We would highly recommend Paul’s place. All rooms were spacious and very nicely furnished. Kitchen had everything you needed to self cater including coffee machine, washing machine and dishwasher. Bathroom was huge and modern with a large shower and plenty of linen provided. Bed was very comfortable. Paul was easy to communicate with and responded quickly to any questions. The location of this Airbnb is first rate. In a quiet and peaceful area within easy walking distance to the high street.

Entire quiet flat town centre - Free parking
What a great stay! Firstly, Geraldine was a fantastic host and was always happy to help - even when she really didn’t need to! Secondly, as far as a small flat can go? It’s a fantastic location that’s close to amenities but still far enough to get a good nights sleep. Would definitely stay here again & recommend it to anyone else!!
Quick stats about holiday rentals that are kid-friendly in Winchcombe
Total rentals
20 properties
Nightly prices starting at
$103 SGD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Wifi availability
20 properties include access to wifi
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- Cotswolds AONB
- Oxford University
- Blenheim Palace
- Silverstone Circuit
- Lower Mill Estate
- Birmingham Airport
- West Midland Safari Park
- Drayton Manor Theme Park
- Cheltenham Racecourse
- Cadbury World
- Ludlow Castle
- Sudeley Castle
- Waddesdon Manor
- Puzzlewood
- Coventry Cathedral
- Bath Abbey
- Bowood House and Gardens
- Lacock Abbey
- No. 1 Royal Crescent
- Royal Shakespeare Theatre
- Shakespeare's Birthplace
- Hereford Cathedral
- Manor House Golf Club
- Painswick Golf Club