Chepstow is a town that is rich in history. Its most popular landmark is the Great Tower of Chepstow Castle, which is one of, if not the oldest surviving stone castles in the UK, having been constructed in 1067 under the command of William FitzOsbern, the first earl of Hereford and an ally of William the Conqueror. You can also visit Chepstow Museum if you want to learn more about the town’s history. If you want to explore more modern attractions, you can head over to the town center, where you’ll find plenty of shops to explore. Find the best Airbnb vacation rentals in Chepstow, UK, by using this list as your guide.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 11, 2024.
1. Pineapple Cottage (from USD 101)
Chepstow is a historical town, and what better way to spend time there than by staying at an equally historical building? This two-bedroom cottage was built sometime in the 17th century. While small, the property is well equipped and comes with kitchen and laundry facilities. It also has a few bonuses, such as board and video games, toys for kids, and toiletries. It even has its own garden.
Catch a glimpse of Chepstow Castle right from this property. Do be aware that you will need to climb stairs to get to the bedroom.
Top guest reviews
Amenities & Room:
nicely furnished equipped with all kitchen appliances you may needthe house alone was worth the trip to chepstow comfortable bed and furniturevery comfortable lovely shower with kitchen area sufficient for self cateringCleanliness:
fabulously decorated very clean and well stocked with towels soap etceverything else was cleanthe space was well equipped clean and wonderfully quirkysuch a clean and lovely space it was so gorgeous and the mystery room is great :)the interior is very beautiful clean and with attention to detailsHost:
fantastic host and housetruly great as a hostjoe is a great host with great communicationjoe was super responsive to all our queriesjoe was a great host - excellent communication - and we would highly recommendRead more reviewsLocation:
beautifully renovated property in a central locationreally nice place to stay central chepstow locationbrilliant place close to everything will be going backthe location could not have been more perfectthe location was spot on right in town yet far back enough that it was peaceful
2. Apartment for two in a beautifully restored Georgian townhouse (from USD 125)
This apartment is in a building called Castle House, which is appropriate considering its proximity to Chepstow Castle. It is furnished with the essentials and has a garden where you can hang out.
Do note that you will need to climb two flights of stairs to get to the unit. Unsure of what places to check out in town and the surrounding areas? Not to worry, because your hosts can provide you with tips on what areas and attractions are worth checking out.
Top guest reviews
Cleanliness:
the apartment is clean well-equipped and comfortable and there is a pleasant outside seating area for fine daysthe apartment was clean homely and in an amazing location surrounded by beautiful walks and lots to doHost:
i highly recommend the host and propertyit had everything we needed and kate was a wonderful host happy to help with anythingthe apartment is perfect for two people and the hosts are very friendly and helpfulkate and family were fabulous hosts and we can't wait to go and stay againwe had such a lovely stay here in chepstow kate was so welcoming and helpfulRead more reviewsLocation:
a great location with off-street parking and walks from the doorbeautifully restored house with apartments and everything you need fabulous location near the castle & river
3. Charming cottage at the center of town (from USD 94)
This cottage is located right in the heart of Chepstow, putting you just a few steps from restaurants, shops, cafes, and pubs, as well as attractions such as Chepstow Racecourse and the Priory Church of St Mary. The castle is also accessible on foot from the property.
The townhouse can accommodate up to four people. Fans are provided to help you keep cool, while heating is available to keep you warm. You can cook your own meals in the kitchen. There are laundry facilities in the building that you can use for free.
Top guest reviews
Amenities & Room:
the two toilets were a bonus and we were very comfortableCleanliness:
great communication and everything is super cleanthe house was spotlessly clean and very well equippedeverything was just as wished and very clean and comfortablevery clean modern and ideally locatedthe house was clean spacious with all essentials providedHost:
a very well equipped venue excellent value for money warm welcoming hoststuart's communication was fast and friendlyRead more reviewsLocation:
good location and decent placeabsolutely lovely house in a perfect location within easy walking distance of everythinggreat location to explore the wye valleya lovely place very quiet and in great central locationhouse right in the middle of town easy walk to all amenities and tesco
4. Carpenters Cottage (from USD 89)
This cozy cottage is good for two people, which makes this a great choice if you want to spend a holiday in Chepstow with your significant other. The rental has its own kitchen. Do be aware that this accommodation has stairs. The property is just a two-minute walk away from the castle and the town center. There’s also free parking here.
Top guest reviews
Amenities & Room:
very comfortable cottage for twowifi would be a great additiononly addition that would be a bonus is wifiCleanliness:
great cottage and very cleanscrupulously clean and lovely attention to detailbeautiful place extremely clean and well looked afterit was clean and tidy and had everything you needwell presented and cleanHost:
the host was quick to respond when contacted - we will definitely have a return visitcharlotte was a great host and showed care when there was a local incidentcharlotte was very friendly and always replied quicklyRead more reviewsLocation:
great location and homely insideclose to many great restaurantsthe location is great and it’s so central to everything in chepstowit's in a great locationstayed whilst working nearby and perfect location
5. Modern cottage close to local attractions
This cottage has free parking on the premises, which is great if you’ll be driving in. What’s even greater is that you will no longer need your car until it’s time for you to leave the town, as local attractions are all a stone’s throw from here, including the castle and the racecourse, as well as shops, restaurants, and pubs.
The rental is fully modernized, featuring central gas heating, a fully equipped kitchen, large TVs, and gaming consoles. Please do be aware that this house is split into two levels, with the bedrooms located on the upper floor.
Monmouthshire, Wales, United Kingdom
224 meters (0.2 ft) from Chepstow Castle / Castell Cas-gwentSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
bedrooms have comfortable beds and extra extra bedding if necessary also plenty of lovely white towelsvery well equipped kitchen parking and great wi-fi and a lovely welcome from robthis is a really lovely spacious apartment fully equipped with everything you could need for your stayCleanliness:
it clean and modern toohi spec very clean and cosy found a hidden little gemthe space was clean and well-stockedit was sparkling clean with everything you needthe house is very clean and well-equippedHost:
friendly and welcoming hostsrobert was a great hostthe host was very helpful & was always on hand to answer any queriesrob was really friendly helpful and easy to communicate withgreat accommodation highly recommended rob was excellent host nothing was to much troubleRead more reviewsLocation:
perfect location in beautiful chepstowexcellent location with pubs/restaurants/riverside within walking distancegreat location and everything you could want in the accommodationamazing location to chepstow walking distance to shops cafes restaurants and pubsa great location if youre travelling by train
6. Quiet room with private bathroom (from USD 57)
Are you a solo traveler? If so, look no further than this rental, which is just right for one. The room for rent has its own bathroom. Tea and coffee-making facilities are thoughtfully provided by the host.
The property is close to the castle. It is also just a short stroll away from pubs, bars, and restaurants. If you’re taking public transport, the train and bus stops are a stone’s throw away as well.
Top guest reviews
Amenities & Room:
susan’s private room is very comfortable with a bathroom just next doorhighly recommended beautiful room in a beautiful home quite and close to all amenitiesthe room is excellent value for moneybathroom was great with a fabulous powerful showerCleanliness:
everything was clean and well keptoh plus lovejoy clean bathroom which i soaked in 2 nights in a rowher home was very clean and the bed was super comfysparkly clean bedroom in a central locationthe room was very clean and decorative as was the bathroomHost:
she was very friendly welcoming and helpful throughoutthe host makes you feel like familysusan is a wonderful hostsusan is a wonderful hostsusan is a great hostRead more reviewsLocation:
lovely place near to the city centregreat little find close to town and the castlea stone's throw away from many restaurants and pubs yet quiet and peacefulsusan very helpful relay made us welcome great location for the race coursealso very close to the high street for a lovely breakfast the next day thanks susan
7. Bed and breakfast by the castle
This rental is perfect for those who love bed and breakfast places. With its cozy decors, this room for four feels just like home. You can enjoy views of the castle from the terrace on the ground floor of the building. You will also enjoy the breakfast provided by the host.
There’s paid parking close to the building. The property’s location allows you to access restaurants, cafes, and pubs even if you’re just on foot.
32 meters (103.4 ft) from Chepstow Castle / Castell Cas-gwentAccommodates: 4
Top guest reviews
Amenities & Room:
beds were goods breakfast so much typical we had a visiting tour of chepstow for freeCleanliness:
place was spotlessly clean and welcomingbedrooms are comfortable and homely and very cleanHost:
glyn and jan made us so welcome in their lovely home and were really good hostsincredible hosts delightful home beautiful settingdr glyn and jan lovely hostsbasic accommodation but glyn is a great hostvery friendly owners who will try their best to make your stay as enjoyable as possibleRead more reviewsLocation:
perfect location for a visit to chepstow and surrounding arealiterally picked us up from the station as we had a huge suitcase with usthe rooms are very comfortable the location in chepstow was great with the castle in the back yardeasy to park nearbylovely location fantastic hosts 10/10
Dive deep into history in Chepstow
Chepstow is a town where you’ll see a slice of history at practically every corner. It also has modern attractions, which makes this a great option if you want to visit a place where you will be educated and entertained. Spend a few days in this town so you can give yourself enough time to dig deeper into its story and enjoy exploring its sights and attractions.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to