The beautiful town of Chepstow attracts tourists for its picturesque countryside and historic sites. The skillfully constructed Chepstow Castle is one of the city’s most iconic sights. It often organises fun activities such as reenactments, live music and theatrical performances. Wye Valley Walk is a beautiful walking route across Wales to discover Tintern’s natural beauty and the county town of Monmouth. Hikers can delve into the 177-mi (284.85-km) Offa’s Dyke Path, a long-distance walking route that offers stunning views of Black Mountains. A trip to Chepstow Racecourse is a must if you enjoy horse racing. Also, live music, race nights and events are held at this historic racecourse, including Coral Welsh Grand National. Chepstow requires a stay long enough to explore its neighbourhood and popular tourist attractions. For suitable accommodations, check out the best long-term rentals near Chepstow, UK.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Family-friendly home, Abergavenny (from USD 442)
This spacious home is ideal for large families and groups with children. The kitchen is a chef’s dream, equipped with all the amenities needed to whip up mouthwatering meals. Indulge in delicious food or a social gathering in the large dining area. Your little ones will be delighted with toys, books, games and an outdoor play area. The office setting and Wi-Fi facilitate business tasks.
Step outside to the enchanting garden, offering a blissful sanctuary. The best part? You can enjoy a generous discount on your stay for seven nights or more.
Top guest reviews
Amenities & Room:
the bedrooms are extremely comfortable and there is lots of outside space with great views across the valleyCleanliness:
lovely living space and was very cleanHost:
sarah and dan are great host provided a the details needed to make our stay comfortableRead more reviewsLocation:
the location was perfect for us
2. Renovated cottage with river views, Lydney (from USD 159)
Experience country life in this well-lit cottage with views of the beautiful River Severn. With all the amenities and conveniences, this rental is an excellent choice for a lengthy break. Further, you can enjoy a generous discount on a minimum stay of 28 nights.
The cottage includes high-quality bedding, laundry facilities, a well-appointed kitchen and a living area with a wood-burning stove. Additionally, there is a television, DVD player and Wi-Fi for endless entertainment.
Free parking is a benefit to navigating around the area. You can relax in the peaceful garden after a long day of outdoor adventures. Your furry friend is welcome too.
Top guest reviews
Host:
we were very comfortable and the owners were very obliging and helpfulRead more reviewsLocation:
good location on the outskirts of the forest of dean
3. The Grooms Cottage, Woodcroft (from USD 114)
This tastefully designed cottage offers free parking and a perfect base for exploring the Lower Wye Valley. You can get great deals on weekly and monthly stays, making it even more enticing.
The premium bedding and room-darkening shades provide a restful slumber. You can stay warm with an indoor fireplace on frigid nights. Relish home-cooked meals from the fully stocked kitchen or delicacies at the local community-owned pub.
The high-speed internet enables remote work while a TV offers leisurely entertainment. You can sip beer on a private patio while admiring the lovely views.
Top guest reviews
Amenities & Room:
enjoyed breakfast with views on the deckingthe cottage was perfect from the comfy beds to the kitchen appliances to the views from the windowthe cottage is also comfortable and equipped with everything you may need during your staywhat a wonderful cottage very comfortable indeed a thoughtful blend of homeliness and stylish features throughoutwonderful place to stay - immaculate and comfortable - beautiful area to be basedCleanliness:
very nice property extremely clean and tidythe cottage is very stylish clean and welcomingit's so clean and beautiful a real home from homeHost:
the hosts were extremely responsive and helpfulamazing place and great host xxvery helpful and communicative hostsour host was kind and the wonderful house reflects great design and tasteit had everything we needed and the hosts were extremely helpfulRead more reviewsLocation:
great location to explorethe location is fabulous for local sights and restaurantsit's in a great location for so many beautiful walkslovely house in a great locationan amazing cottage which we would highly recommend great location and very friendly people
4. Old manor house, Mathern (from USD 624)
Choose this historic house where aesthetics meet comfort and take advantage of special monthly stay discounts. The fully equipped kitchen with a dishwasher, microwave and refrigerator is available for effortless meal preparation. Added facilities of a washing machine, dryer and iron ensure a hassle-free extended stay. With cosy bedrooms, kid-friendly amenities, a TV and Wi-Fi, your every need is catered to.
Enjoy the convenience of on-site parking, while the spacious garden is perfect for relaxing and making joyful memories with your little ones.
Top guest reviews
Amenities & Room:
beds were comfortable although don't forget some of them are sofa bedsa very special place hugely characterful great for families with rooms spread across 3 floorscomfortable beds and nice linen nice fireplace which we enjoyed in the eveningswe had breakfast and lunch in the garden and love every moment of our staygreat equipped kitchen stunning garden and very comfortable bedsCleanliness:
charming spacious lots of extra little touches kids and dog loved exploring the house and gardenHost:
thank you linda for being such a kind hostas a host linda was extremely welcoming and helpful with her homelinda was very responsive and helpfullinda is incredibly helpful and responsivelinda let us check out late which was so kindRead more reviewsLocation:
we walked into chester which is about 40 mins easy walkenchanting house and a beautiful location to spend the weekendperfect place for a family reunion in close proximity to bristola lovely quirky manor house which was a perfect location for a family weddinggreat house great location and lovely host
5. Fisherman's Rest, Abergavenny (from USD 145)
Visit this two-story cottage to get a taste of farm life. The nearby river is a great place to go for a stroll or to fish. You can cook tasty recipes with freshly caught salmon in the complete kitchen. The effective heating system allows you to stay toasty in the winter. Other conveniences include a washing machine, a TV for entertainment and a dining area for enjoyable meals.
Internet access helps you work and stay connected with loved ones, especially during extended visits. Moreover, the free parking and irresistible monthly discounts further increase the allure.
Top guest reviews
Amenities & Room:
good wifi and tv hot shower full size hob/oven/grill fridge and microwavemy 3 year old son loved the space and enjoyed having his own bedroom and adult sized bedthe cottage was spacious and very comfortable and we were really impressed with the attention to detailCleanliness:
the barn conversion was very clean and comfortable and had everything we neededfisherman's rest is a beautiful cottage spotlessly clean and spacious for threeHost:
lovely place with lovely hostshost tracey was very helpful and approachabletracey was a lovely host and very thoughtfultracey was a responsive friendly and attentive hostvery friendly hosts with daily greetings from the farm dogsRead more reviewsLocation:
the location was perfect - an easy drive from the m4 but in the middle of beautiful countrysidethis is such a wonderful spot for a peaceful break close to the mountains and beautiful welsh countrysidethat area was an easy 30 min drive away and we also had a great walk up therewe were interested mainly in wildlife and country walks and the location is ideal for thatwe loved the location (for walks birdwatching and photography) and the accommodation is very good value
Superhost
6. Oakgrove Holiday Cottage, Brockweir Common (from USD 119)
This rural cottage offers a serene vibe with abundant wildlife and outdoor pursuits. Savour delicious meals prepared in the modern kitchen before retiring to the cosy bedroom for a restful night’s sleep. The complimentary internet access allows you to work or browse at your convenience. The private patio and yard are the best spots to chill and take in the breathtaking hues of the sky.
As the cottage is situated amidst rolling hills, having your car and access to free parking are advantageous. Additionally, don’t miss the fantastic monthly savings offered here for long-term stays.
Top guest reviews
Amenities & Room:
the cottage is cosy comfortable and fully equippeda lovely small but well proportioned one level property having all the usual facilities for a self-catering holidayCleanliness:
it was immaculately clean well equipped extremely comfortable and in a stunning locationclean and comfortable cottage peaceful location and wonderful wildlifethe property is immaculately clean and is equipped with everything you could possibly need for an enjoyable stayHost:
gina and paul were wonderful hostshosts are very friendly too and make sure you're settled ineasy check-in and great hoststhey made us feel very welcome and were very friendly and helpfula lovely cosy cottage in a fantastic location with friendly and helpful hostsRead more reviewsLocation:
the remote location offers peace and solitudeit's a great locationnice little property in great locationthere is a village shop which is well stocked and has a cafe that does amazing homemade cakewe highly recommend this place for an unforgettable break to unwind and recharge
7. Cosy cottage in Brecon Beacons (from USD 108)
Nestled in a picturesque location, this thoughtfully-designed cottage makes excellent use of its features. Guests can enjoy the convenience of free parking and easy access to local pubs’ delectable food. In addition, the cottage provides tempting monthly discounts for long-term stays.
The double bedroom on the first floor exudes warmth with its oak beams and is outfitted with extra pillows, blankets and room-darkening shades. The well-equipped kitchen and in-unit washer and dryer are convenient for extended visits.
A TV and sound system are available for entertainment, while the dedicated workspace and Wi-Fi facilitate remote work. The patio and outdoor furniture with a fire pit are the perfect spots to barbeque and spend time with loved ones.
Top guest reviews
Amenities & Room:
beautiful views and a cozy comfortable interiorthe cottage is very comfortable particularly the bedroom and the lounge - both upstairs but on different levelsa comfortable and cosy little place nestled on the edge of the beautiful brecon beacons with stunning viewswould highly recommend this place very relaxing with lots of comfortable walks in the areaCleanliness:
beautiful place extremely clean and tastefully decoratedgreat decor and very clean with everything you would expect and morethe barn was super clean and had everything we neededthe accommodation itself was immaculately cleanbeautiful little spot super clean and everything we wanted for a perfect weekend getawayHost:
hosts were helpful with really quick responsesalan and helen were great hostshosts are lovely and are excellent at communicating and responding to questionshosts are very accommodating and friendlyhelen and alan were most welcoming and helpfulRead more reviewsLocation:
a really good locationi loved the kitchen - so cute really lovely location - so nice and peacefulif you're looking for an escape from city life this is the perfect placea really beautiful annex even better in person the ideal location for a countryside getawayit was really well located in a pretty quiet area with just sheep and birdsong for company
8. Renovated cottage with modern amenities, Wainfelin (from USD 81)
This lovely three-bedroom cottage has an attractive attic and other conveniences for a pleasant experience. Moreover, there are amazing deals for prolonged visits.
You can use a fully equipped kitchen for convenient meal preparation or have tasty treats at the nearby chip shop and pub. Stay connected with free Wi-Fi and enjoy your favourite shows on TV. You can relax and read by the cosy electric fireplace or venture out to explore the area with the convenience of free parking. Your animal companion is also welcome here.
Top guest reviews
Amenities & Room:
also wifi was great especially with the kidscomfortable beds and nicely equipped kitchenyet another lovely stay at gill's cottage wonderful breakfast provided and quiet comfortable sleepthe attic room is amazingthe place was very neat and comfortableCleanliness:
really clean and was roasting hotquirky cozy clean comfy cottagethe place is clean comfortable and warmvery clean and tidy property with all the essentials availableevery last detail was thought about and place was very cleanHost:
thank you for being a good hostgreat host quick to respond and send informationperfect host with exceptional choice of condiments and foodfabulous place to stay and wonderful hostwould highly recommend this property and this hostRead more reviewsLocation:
ideal location and very homelyideal location for visiting my familylocation was really good big tesco is close bylocation is peacefull quite and easy access to public transport toolovely pub a very short walk away and tesco not too fair either
9. Lovely stone cottage with fireplace, Caerleon (from USD 205)
This cottage is ideally located among a wide range of bars and restaurants and is just a short drive from The Celtic Manor Resort - perfect for an unforgettable family day out. Take advantage of the ease of free parking and tempting discounts on monthly stays.
You can whip up delightful meals in the open-plan kitchen with a refrigerator, microwave and crockery. Additionally, the convenience of a washing machine keeps your favourite outfits fresh.
You can stay cosy on chilly evenings thanks to the fireplace and log burner in the living room. There is a lovely patio and garden to unwind on. Additionally, your pet is also welcome to participate in the fun.
Top guest reviews
Amenities & Room:
telephone signal is erratic but wifi is goodthe cottage is well equipped with a good wifi signalvery comfortable and plenty on amenitieswe had enough parking space the beds were comfortable and the cottage was charmingnice big bath tub comfy double bed lovely scenic views from the upstairs windows in the morningsCleanliness:
very comfortable clean and well appointedaccommodation spot on clean and exactly as per the picturesbeautiful property cleaned to a lovely standardreally comfortable clean and well equipped homeHost:
the hosts where absolutely lovely & couldn’t help enoughowners very friendlythe hosts were friendly and super helpfulwelcoming hosts rob and anne on hand to help at all timesrob and anne are such welcoming and friendly hostsRead more reviewsLocation:
nice location ideally located for caerleonexcellent location 20 minutes walk to the village and 35 minutes walk to a fantastic tapas restaurantlovely quiet location walking distance to the centre of carleon and 5-10 drive to celtic manornice location lots of interesting things nearby and convenient local servicesidyllic location and wonderful hosts
10. Three-bedroom cottage with valley view, Tintern (from USD 151)
This rental boasts a conservatory overlooking a picturesque garden and enchanting woods. Further, you can enjoy special monthly savings for a memorable getaway.
Bask in the natural beauty as you dine on the outdoor patio, savouring delicious grilled meals with the soothing sounds of Angiddy River. Inside, you will find cosy bedrooms, a well-equipped kitchen and kid-friendly amenities to make your extended stay comfortable.
You can unwind by watching TV, listening to music or snuggling up near the fireplace with a captivating book. Wi-Fi and a dedicated workplace cater to your business needs. With free parking, embark on thrilling adventures exploring Monmouthshire and Brecon Beacons.
Top guest reviews
Amenities & Room:
fabulously comfortable cottage with stunning viewswell equipped kitchen and delightful views over the forestthe house was really comfortable with lovely viewsthe cottage has everything you would need for a comfortable staythe cottage is well stocked/equipped particularly impressed by the kitchen appliances and accessoriesCleanliness:
clean and tidy cottage with all the crockery and cutlery you'll need for your stayit was spotlessly clean extremely comfortable and included everything we needed for our staythe cottage was immaculately clean and very well equippedthe cottage is clean and as shown in the picturesHost:
the host is very helpfulour host was very helpful throughout with excellent communicationjane was a great host and ensured we had all the information before we arrivedjane was helpful thoughtful and on-hand with advice and suggestions throughoutjane is a friendly kind and accommodating host and went out of her way to helpRead more reviewsLocation:
the location is fantasticgreat location for trail running and cyclingexcellent location to explore the local areafabulous location and gorgeous garden to relax inperfect proximity to explore tintern being able to walk down to all the attractions and pubs
Enjoy a fun-filled getaway in Chepstow
With a variety of outdoor activities, cultural experiences and natural wonders to explore, Chepstow promises an unforgettable adventure for every visitor. Pick any of the above rentals for extended stays and lucrative offers.
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