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Chepstow villas
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25 Villa rentals in Chepstow

Search Vacation Homes near the Old Town in Chepstow

Live like a local by renting central vacation homes in Chepstow, putting downtown restaurants right outside your door.

Self-contained Annexe, Chepstow - Chepstow
9.8 64 reviews

Self-contained Annexe, Chepstow

house
This private guesthouse is located in central Chepstow, a 7-minute walk from the town center and within easy reach of Chepstow Racecourse, the Wye Valley, the River Wye, and Chepstow Castle. Guests consistently rate this property excellent for its location, cleanliness, and overall experience.
This one-bedroom, one-bathroom annexe comfortably accommodates two guests. Amenities include a private entrance, ensuite shower room, tea and coffee making facilities, DAB radio, and free on-street parking within a 3-minute walk.
Chepstow Town. Welsh Cottage. - Chepstow
9.9 302 reviews

Chepstow Town. Welsh Cottage.

house
This home is located in the heart of Chepstow, just a short walk from the castle, Priory Church, racecourse, and river, and within easy reach of the AONB Wye Valley and Forest of Dean. It has received excellent ratings for location, cleanliness, and overall experience. This charming home offers two bedrooms and one bathroom, comfortably accommodating up to four guests. The home features a fully equipped kitchen, a spacious living room with a dining table, and a separate sitting room with comfortable seating and a TV.
Richmond House Apt 2 - Chepstow
9.1 15 reviews

Richmond House Apt 2

house, Chepstow
Apartment 2, a Chepstow vacation rental, is conveniently located 14 miles from Bristol Parkway Station and 17 miles from Cabot Circus, offering easy access to both transportation hubs and attractions.
This 220-square-foot (approximately 20-square-meter) one-bedroom, one-bathroom unit sleeps three guests and features a fully equipped kitchen, free Wi-Fi, private parking, and a flat-screen TV.
Charming 4-bedroom Cottage In Historic Chepstow - Chepstow
10 3 reviews

Charming 4-bedroom Cottage In Historic Chepstow

cottage, Chepstow
Vauxhall Cottage, a three-bedroom home in Chepstow town, is a five-minute walk from the historic center, Chepstow Castle, and the River Wye.
This 1,900-square-foot vacation rental sleeps six, features a fully equipped kitchen with a dishwasher and microwave, a private garden with a BBQ, and off-street parking for multiple cars; nearby attractions include the Chepstow Racecourse and easy access to the M4/M48/M5 motorway network.

Best family friendly Chepstow villas and beach houses

Among the 25 accommodations in Chepstow, here are the 4 best family friendly villas and beach houses

Orchard View By Cliftonvalley Apartments - Chepstow
No reviews

Orchard View By Cliftonvalley Apartments

house, Winterbourne
Orchard View by Cliftonvalley Apartments in Winterbourne offers convenient access, located 1.7 miles from Bristol Parkway Station and 6.3 miles from Cabot Circus.
This 60-square-foot house accommodates up to 11 guests across 4 bedrooms and features a kitchen with a fridge, microwave, and dishwasher, a Jacuzzi, a garden, and parking, with a check-out time of 11:00 AM.
Edge Barn - Chepstow
9.7 181 reviews

Edge Barn

house, Woolaston
Edge Barn is located in Woolaston, just 18 miles from Bristol Parkway Station and 23 miles from both Bristol Temple Meads Station and Bristol Cathedral, making it a great base for exploring the surrounding countryside. Guests consistently rate the house excellent for location, cleanliness, and overall experience.
The vacation home has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests in its 1180 square feet of space. Amenities include a fully equipped kitchen, a private garden, free Wi-Fi, parking, and stunning river views from the patio.
The Studio - Chepstow
9.7 154 reviews

The Studio

chalet
This studio apartment is located in a peaceful rural setting near Chepstow, just a 5-minute drive from shops and a 40-minute drive from both Bristol and Cardiff. It has received excellent ratings for its location, cleanliness, and overall experience.
The studio is a self-contained unit with a private garden and off-road parking for two guests. It includes a modern kitchen with appliances, a cozy living area with a fireplace, and a bedroom with a king-size bed. A travel cot is also available for families with young children, making this a great option for exploring the nearby Forest of Dean, Wye Valley, and long-distance hiking trails.
Medieval Manor For Group Stays! - Chepstow
9.9 107 reviews

Medieval Manor For Group Stays!

castle
The Medieval Manor is located in the historic village of Caldicot, near the M4 & M5 motorways, making it easily accessible from major roads. The manor has received excellent ratings for its location, cleanliness, and overall experience.
The manor sleeps up to 12 adults in bedrooms with additional sofa beds and single mattresses available for larger groups or families. Guests have access to a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, along with a garden, parking, and internet.

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Best Chepstow houses with a garden

Well House By Cliftonvalley Apartments - Chepstow
10 1 review

Well House By Cliftonvalley Apartments

house, Bristol
Well House by Cliftonvalley Apartments is located in Bristol, 2.7 miles from Bristol Parkway Station and 6.9 miles from Cabot Circus and Bristol Cathedral.
This 1570 square foot apartment offers 6 bedrooms, 5 bathrooms, a full kitchen with a dishwasher, free WiFi, and private parking, accommodating up to 19 guests.
Ferryman's Lodge, Romantic, Character Holiday Cottage In Brockweir - Chepstow
No reviews

Ferryman's Lodge, Romantic, Character Holiday Cottage In Brockweir

cottage, Chepstow
This cottage rental in Chepstow is located in Brockweir within the Wye Valley National Landscape, just 1,056 feet from the River Wye and 0.2 miles from the Brockweir Country Inn and Kingstone Brewery.
This 970 square foot lodge accommodates two guests and features an open-plan living space with a woodburning stove, a non-enclosed veranda with furniture, lawn space, and off-road parking for one car.
Orchard Cottage Monmouthshire - Chepstow
10 1 review

Orchard Cottage Monmouthshire

house, Saint Arvans
Orchard Cottage, a holiday home in Saint Arvans, Monmouthshire, is located 16 miles from Bristol Parkway Station and 31 miles from Bristol Airport, providing easy access to Bristol's attractions.
This cozy one-bedroom cottage accommodates two guests and features a fully equipped kitchen, a private garden with a barbecue, and free WiFi, with nearby opportunities for golfing, fishing, and cycling.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chepstow
9.7 36 reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Woolaston
The Piggery is a unique cottage located in a secluded meadow near the village of Woolaston, Gloucestershire, offering stunning views of the River Severn and the rolling countryside.
This 1,400 square foot cottage, originally a pig barn, offers a charming and unique experience for those seeking a different kind of holiday accommodation, with three bedrooms, a fully equipped kitchen, and a private garden, perfect for families or groups of up to five guests.

Best Chepstow houses with parking

The Old Pump House - Chepstow
8.0 10 reviews

The Old Pump House

house, Lydney
The Old Pump House is located in Lydney, Gloucestershire, a short distance from Bristol and its attractions, with Bristol Parkway Station being 21 miles away. The house has excellent user, location, and cleanliness ratings.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. The 1850 square foot house has a patio, garden, and barbecue facilities, along with a fully equipped kitchen, free Wi-Fi, a flat-screen TV, and free parking.
The Potting Shed At Mathern Palace - Chepstow
9.0 2 reviews

The Potting Shed At Mathern Palace

cottage, Mathern
The Potting Shed is located in Mathern, a village in the Welsh countryside, close to Chepstow and within walking distance of the Millers Arms pub.
This two-bedroom cottage, located on the grounds of the historic Mathern Palace, offers a comfortable living space with a modern kitchen, a Smart TV with streaming services, and a private garden.
Gardeners Cottage At Mathern Palace - Chepstow - Chepstow
10 2 reviews

Gardeners Cottage At Mathern Palace - Chepstow

cottage, Chepstow
This Chepstow cottage rental is conveniently located near St. Pierre Country Club (0.8 miles), Chepstow Castle (under 2 miles), and Chepstow Racecourse (1.9 miles), offering easy access to local attractions.
This two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen with a refrigerator, microwave, stovetop, and oven, a washing machine, a smart TV, and a peaceful garden.
Welsh Gatehouse: Historical Castle With Ev Charger - Chepstow
9.9 209 reviews

Welsh Gatehouse: Historical Castle With Ev Charger

castle
This charming castle is located just 1.5 kilometers from St. Pierre Country Club and within 5 kilometers of both the River Wye and Chepstow Castle, offering a peaceful escape from the town's bustle. Guests consistently rate this castle as excellent for location, cleanliness, and overall experience.
This one-bedroom castle provides 590 square feet of space, comfortably accommodating two guests. Enjoy a peaceful garden, barbecue grills, and convenient amenities like a fridge, freezer, microwave, and a terrace.

Check Out Vacation Homes with a Pool in Chepstow

Enjoy a proper swim in the heart of the city. These vacation homes in Chepstow include pool access for your daily routine.

La Villa Olli -Natural Pool & Jacuzzi - Chepstow
9.9 75 reviews

La Villa Olli -Natural Pool & Jacuzzi

house, Bristol
Cottage ∙ 4 Bedrooms ∙ 10 Guests - Chepstow
10 4 reviews

Cottage ∙ 4 Bedrooms ∙ 10 Guests

cottage, Pilning
The Old Rectory - Chepstow
9.7 3 reviews

The Old Rectory

house, Bristol
The Honey Pot - Chepstow
9.9 35 reviews

The Honey Pot

house, Chepstow

Search 5-Star Holiday Houses in Chepstow

For those who appreciate quality, these high-end vacation homes in Chepstow deliver premium comfort on every front.

Willow Lodge - Chepstow
9.9 63 reviews

Willow Lodge

cabin

Find the Best Holiday Houses with Jacuzzi in Chepstow

A vacation home with private hot tub access after a day in the city is a luxury detail that makes your stay in Chepstow truly memorable.

The Honey Pot, Romantic, With Hot Tub In Chepstow - Chepstow
No reviews

The Honey Pot, Romantic, With Hot Tub In Chepstow

cottage, Chepstow
Spacious Detached House With Garden & Parking - Chepstow
No reviews

Spacious Detached House With Garden & Parking

house, Bristol
Hidden Well - Chepstow
9.0 6 reviews

Hidden Well

house, Bristol
The Nook - Chepstow
10 1 review

The Nook

house, Tidenham
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