House vacation rentals in Chepstow

Find and book unique houses on Airbnb

Quick stats about house rentals in Chepstow

  • Total vacation rentals

    Explore 20 vacation rentals in Chepstow

  • Nightly prices starting at

    Chepstow vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Chepstow vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chepstow rentals

  • 5 Average rating

    Chepstow stays are highly rated by guests—averaging 5 out of 5!

Top-rated house rentals in Chepstow

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of the barn conversion is shown, featuring a mixture of stone and wood materials. Bright flowers and greenery surround the entrance, along with patio seating. Large windows allow natural light to illuminate the interior, and a red front door offers an inviting focal point.
Home in Falfield

The Barn. Perfect for family & friends to meet up.

This very spacious barn conversion is the perfect place to meet family & friends, to relax and “re-connect”. The large fully equipped open plan kitchen and dining room join into the light and comfortable lounge to form the perfect social space plus there's a games room with full size table tennis! Extensive outside patios & gardens provide stunning views over the Severn Vale and wonderful sunsets. Three of the four bedrooms are on the ground floor; all have private en-suites with shower or bath.

FamilyLocationKitchen

4.99 out of 5 average rating, 210 reviews
Top guest favorite
The entrance of a modern bungalow is framed by lush greenery, showcasing a welcoming wooden front door. Two stone planters with vibrant flowers add a touch of color to the entrance, set against a neatly maintained lawn and light-colored stone pathway.
Home in Llanvaches

The Sheiling | Countryside Escape with Hot Tub

Countryside home renovated to a high standard in the village of Llanvaches on the edge of Wentwood Forest, the largest ancient forest in Wales. Located between Newport and Chepstow, The Sheiling has views over the open countryside and is perfect for a relaxing getaway offering peaceful forest walks, scenic views, and exploring the exceptional beauty and attractions of the surrounding area. Our local pub/restaurant is a short walk down the lane and there are a variety of traditional pubs nearby.

ValueFamilyGrill

4.99 out of 5 average rating, 215 reviews
Top guest favorite
Home in Monmouth

Offa's Hideaway - Wye Valley

Offa's Hideaway is an idyllic and peaceful retreat on Offa's Dyke footpath in the village of Redbrook. Enjoy the private patio and veranda overlooking the Wye Valley woodlands, with a BBQ and petanque court. Recently renovated to a high standard it includes an open living and kitchen area with Emma Sleep king sofa bed, dual aspect bedroom with king bed, and modern bathroom with large deluxe shower. The space has private parking accessed via a magical woodland path with atmospheric lighting.

FamilyLocationAccess

4.94 out of 5 average rating, 106 reviews
Top guest favorite
The traditional cottage is partially obscured by lush greenery, featuring a white exterior and prominent chimneys. A conservatory is visible, and trees frame the surroundings, creating a tranquil and inviting setting in the heart of nature.
Home in Trellech

Cute little Wye Valley cottage

Surrounded by woodland with hilltop views across the Wye Valley to Offa’s dyke, this eco friendly traditional Monmouthshire cottage is the perfect place to unwind and enjoy nature at its very best. Spend time in the garden listening to bird song and the gentle babbling of the stream or step out the gate to explore Cleddon Falls and beautiful view points along the Wye Valley walk. The medieval village of Trellech and Tintern Abbey are also within easy reach off or on road by foot, bike or car.

LocationValueLayout

5.0 out of 5 average rating, 134 reviews
Top guest favorite
The exterior of a charming stone cottage is presented, featuring a warm facade adorned with ivy. A welcoming entrance opens into the space, while a small courtyard area is visible, surrounded by greenery and gravel pathways, enhancing the tranquil atmosphere.
Home in Tidenham Chase

The Dairy

Take it easy at this unique and tranquil getaway. Set in the Wye Valley, an area of outstanding natural beauty. You can walk/cycle for miles without touching a road. Collect eggs, milk and ice cream from the farm next door Tintern Abbey with its pubs and restaurants is a walk away (an hour); the races, music at the Castle, Clearwell Caves, Puzzlewood, steam train.. and more. Travelling with friends/family? Check our other listing within the same grounds: airbnb.com/h/cosy-wye-valley-getaway

ValueFamilyHiking

4.92 out of 5 average rating, 177 reviews
Guest favorite
The exterior of a charming self-catering cottage features a whitewashed façade, wooden accents, and a welcoming front porch. A small stone path leads to the entrance, surrounded by a well-maintained garden with various shrubs and a seating area. Natural scenery frames the cottage in the background.
Home in Coed-y-paen

Forest Cottage

There are no hidden extra payments, the nightly fee is total. Self catering cottage, originally built in the 1800's, restored and extended to provide a high standard of accommodation. Set in private gardens which extend to 23 acres and with outstanding views across the Usk valley. The garden area provides 2 large decked viewpoints, Private parking. The property has retained its original stone spiral staircase which might prove difficult for guests with mobility issues or the very young.

ValueFamilyOutdoor spaces

4.96 out of 5 average rating, 323 reviews
Top guest favorite
Home in South Gloucestershire

Cotswolds Romantic Getaway in Luxury Barn

The Barn at Church View is a unique luxury conversion of a 200 year old stone former calving barn on the western fringe of The Cotswolds, near the maket towns of Thornbury and Wotton-under-Edge. Its privileged countryside location is within easy reach of the vibrant cities of Bristol, Bath and Gloucester offering an abundance of things to do. The recently renovated barn is a tranquil private space away from noisy roads, the perfect setting for your next holiday or romantic getaway.

ValueFamilyWalkability

4.95 out of 5 average rating, 224 reviews
Top guest favorite
The exterior of the cottage is shown, featuring a two-story structure with stone and rendered walls. Windows in varying sizes are highlighted, and a front door is centered under a small awning. Flower beds with vibrant blooms enhance the entrance, with lush greenery surrounding the property.
Home in South Gloucestershire

Entire House . Self Catering . Almondsbury

Roylands Farm Cottage is located on a working farm, surrounded by countryside yet easy access to motorway networks. Ideally located for exploring Bristol and surrounding areas. The property allows sole use of entire house. The property has 5 bedrooms, four with en-suites, a family bathroom, a lounge with conservatory, Kitchen dinner with all cooking facilities available. A large private garden, with outdoor seating, BBQ and pizza oven for you to enjoy. Ample off road parking.

FamilyLocationGrill

4.97 out of 5 average rating, 121 reviews
Top guest favorite
The main entrance features a solid light gray door with a decorative window and a traditional door knocker. A wall-mounted lantern provides illumination, while a small basket of flowers adds a welcoming touch at the base. The cottage number is displayed beside the door.
Home in Aylburton

Cosy cottage in village centre.

Newly renovated and restored to a very high standard, the cottage has retained its traditional features.It is warm and cosy located in the centre of the popular village of Aylburton. Enclosed rear terrace and secure bike storage. The fitted kitchen is fully equipped with everything you need to prepare meals, having said that, there's a great pub next door. There is also a BBQ and outdoor seating, just a step up from the kitchen to enjoy a morning coffee on the sunny patio.

FamilyLocationBiking

4.96 out of 5 average rating, 176 reviews
Guest favorite
Home in Cotham

Redland Suites: The Mews. Great Location & Sleep 4

This beautiful 2-bedroom high spec mews house sleeps 4 guests comfortably. A gorgeous open plan fully equipped kitchen and living area, two bedrooms with king sized beds, both have luxury en-suite bathrooms one with a waterfall shower and the other with a bath. The property also has a downstairs toilet and utility room. These are just some of the features to make your stay perfect. The high-end finish and furniture has been selected with your comfort in mind.

ValueFamilyCheckout

4.94 out of 5 average rating, 107 reviews
Guest favorite
A spacious living area features large windows that invite ample natural light, showcasing views of greenery outside. A comfortable sofa and an orange armchair are present, positioned beside a modern flat-screen television. A dining table can be seen in the background, enhancing the open layout.
Home in Bath and North East Somerset

Bath Stone Retreat | City Views + Free Parking

Immaculately presented two bedroom property located moments from the bustling city streets. This stunning property has the most beautiful views from the terrace, overlooking the UNESCO city of Bath, large living and dining spaces, two bedrooms both with ensuite bathrooms and off street parking. A real gem in the tranquility of elegant Widcombe with an abundance of local cafes, shops, pubs and restaurants only a short stroll away. Come, refresh and relax!

LocationFamilyPets

4.98 out of 5 average rating, 117 reviews
Guest favorite
A spacious bedroom features a floral-patterned bedspread and two black accent pillows on a comfortable bed. Soft carpet covers the floor, complemented by bedside tables with matching lamps. A decorative mirror and a unique light fixture add contemporary charm to the room.
Home in Tutshill

Delightful 3-Bedroom cottage with log burner

1 Park View is a recently renovated 19th century cottage, located in the peaceful Gloucestershire village of Tutshill. The town of Chepstow is only a 10 minute walk away crossing over the Welsh border via the old Wye Bridge (1816). It's a great location if you're looking for a break in the countryside with plenty to explore in the Forest of Dean as well as the beautiful Wye Valley (AONB) and only a 5 minute walk from the Offa's Dyke national trail.

FamilyLocationWifi

4.93 out of 5 average rating, 101 reviews

Popular amenities for Chepstow house rentals