House vacation rentals in Chepstow

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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.

ValueFamilyHospitality

4.99 out of 5 average rating, 209 reviews

Top guest favorite

Home in Parkend

Colliers Cottage at The Barracks, Forest of Dean

Situated in the heart of the Forest of Dean, you will find Colliers Cottage. An ex-colliers cottage that has been extensively renovated in 2024, it comprises 2 bedrooms (1 with en-suite), family bathroom, kitchen, lounge (with sofa bed), dining room and a large, fully fenced private garden with off road parking If you want a stay where you are surrounded by nature, look no further! This is an ideal location for keen walkers, runners and cyclists with off road trails just a short distance away

FamilyValueIndoor spaces

4.99 out of 5 average rating, 138 reviews

Guest favorite

The Georgian home is set within a spacious green lawn, surrounded by mature trees. Its two-story white façade features large windows and a front porch, inviting natural light. The well-maintained garden complements the home's classic charm, providing a serene outdoor space.

Home in Monmouth

Monmouth Georgian owned by our family since 1923

Spacious and charming Georgian home with private garden and parking. Easy 12 min. walk into historic Monmouth town centre with diverse shops, restaurants and supermarkets. Our home has been in our family since 1923 and retains many original features but updated to suit modern comfort and needs. Great access to beautiful surrounding region of Wye Valley and Forest of Dean. Our home boasts a well-appointed kitchen (with AGA), fast internet, sunroom and huge windows that fill the house with light.

FamilyValueLong stay

4.91 out of 5 average rating, 136 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.

FamilyValueKitchen

5.0 out of 5 average rating, 125 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

FamilyLocationHiking

4.92 out of 5 average rating, 175 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.

LocationFamilyHospitality

4.96 out of 5 average rating, 320 reviews

Guest favorite

A spacious converted cidermill is set against a backdrop of green hills. Large windows on the front allow ample natural light into the structure, framed by neatly trimmed hedges and an open lawn area, creating a serene rural setting.

Home in Monmouthshire

Cider Mill Monmouthshire.Views of Black Mountains

Beautiful converted Cidermill set in the Wye Valley, with stunning views of the Black Mountains, quiet rural location three miles from the historic town of Monmouth, therefore we are not suitable for party people. Also not far from The Forest of Dean and the mountain bike tracks, Ideally situated for country walks, comes with ample parking space for two or three cars. Short drive to several country inns and restaurants. What three words compound.quantity.roadways will bring you direct.

LocationValueAccess

4.95 out of 5 average rating, 290 reviews

Top guest favorite

A semi-detached cottage is surrounded by a large grassy area, bordered by wooden fencing. The rear patio features outdoor seating, and a pathway leads to the entrance. Nearby, leafy trees and the natural landscape of the Cannop Valley are visible.

Home in Cannop

Oakwood Cottage, Cannop in heart of Forest of Dean

A 100-year old, semi detached cottage, set in the beautiful Oak woodlands of the Cannop Valley Nature Reserve. The family Cycle trail, XC trail, Enduro trail, DH trail and Pedalabikeaway Cycle Hire Centre are only 200 metres from the cottage. Cycle storage is available at the Cottage. Beechenhurst Lodge Picnic site, the Sculpture trail and the scenic Cannop Ponds are a short woodland walk away. Oakwood Cottage sleeps up to 7 guests and is pet friendly with a large enclosed garden.

ValueLocationCleanliness

4.89 out of 5 average rating, 208 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.

LocationFamilyBackyard

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.

FamilyLocationComfort

4.96 out of 5 average rating, 175 reviews

Top guest favorite

A spacious stone cottage is surrounded by lush greenery, with a pathway leading to the entrance. The exterior features a mix of stone and wood elements, creating a rustic charm. Large windows allow natural light to brighten the interior spaces.

Home in Whitebrook

Adjoined Stone Cottage Wye Valley (Five Springs)

Self-catering cottage in a small quiet Wye Valley village in in the hills above Monmouth. Set in 6 acres of woodland and hidden gardens. Large bedroom with comfortable king (60") & single bed, lounge with log burner, TV & WiFi. Stunning large spa room with sauna, shower, jacuzzi & small toilet room. Kitchen with induction hob, grill and fan oven, microwave, washing machine, tumble dryer and fridge freezer, separate bathroom with toilet.

LocationValueGetting around

4.95 out of 5 average rating, 1150 reviews

Top guest favorite

The side of a spacious barn conversion is shown, featuring large glass doors that provide expansive views of the surrounding fields. Lush greenery and blooming flowers line the foreground, creating a natural border against the rustic stone structure.

Home in Tidenham

Elegant Family-Friendly Retreat Stunning Views

Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean. The perfect getaway for your family and friends. This stylish and spacious barn conversion offers everything you need for a memorable stay, with breathtaking views, incredible outdoor adventures, and plenty off site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. Nightly rate includes 15% Airbnb fee

FamilyValueAccuracy

4.93 out of 5 average rating, 137 reviews