Search holiday beach houses in Chepstow from 100+ sites!

25 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chepstow villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

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.
Vauxhall Cottage, Chepstow - 4 Bedroom Pet-friendly Home With Private Fenced Garden, Walk To Town And Castle - Chepstow
9.9 11 reviews

Vauxhall Cottage, Chepstow - 4 Bedroom Pet-friendly Home With Private Fenced Garden, Walk To Town And Castle

house, Chepstow
Charming Chepstow Cottage, a 18th-century home, is located in Chepstow, Wales, 13 miles from Bristol Parkway Station and 17 miles from Cabot Circus in Bristol.
This three-bedroom, two-bathroom house offers 1810 square feet of space, comfortably accommodating up to 11 guests with amenities including a fully equipped kitchen, private garden with barbecue, free Wi-Fi, and free parking.
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.
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.

Best family friendly Chepstow villas and beach houses

Among the 25 accommodations in Chepstow, here are the 1 best family friendly villas and beach houses

Broadrock Accommodation - Clock Cottage - Chepstow
9.7 154 reviews

Broadrock Accommodation - Clock Cottage

apartment, Chepstow
This Chepstow apartment is located in the Wye Valley, a scenic area with stunning views, just a 40-minute drive from Bristol and Cardiff. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment is perfect for families and pet owners, offering a comfortable and spacious layout with a private terrace or balcony and a garden. Guests can enjoy a fully equipped kitchen, internet access, and a range of amenities like a fitness center, tennis court, and parking, as well as nearby restaurants.

Frequently Asked Questions about villa rentals in Chepstow

Popular destinations

Best Chepstow houses with a garden

The Nook - Farm Stay With Hot Tub - Chepstow - Chepstow
10 8 reviews

The Nook - Farm Stay With Hot Tub - Chepstow

cabin, Chepstow
This Chepstow vacation rental is conveniently located an 8-minute drive from the River Wye and a 4-minute drive from Symonds Yat Rock, offering easy access to scenic walks and stunning viewpoints.
The 300-square-foot (approximately 28-square-meter) cottage features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, a Jacuzzi, and free Wi-Fi.
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.
Offas Dyke Cabin - Chepstow
9.5 151 reviews

Offas Dyke Cabin

cabin
Offas Dyke Cabin is located near Sedbury, a short walk from a local pub and 5 minutes from Chepstow town center, offering easy access to shops, restaurants, and the historic Chepstow Castle. The cozy cabin features a double bed and two single beds, comfortably accommodating up to four guests. The cabin includes a bathroom with a hot shower, a microwave, kettle, toaster, and a small table and TV for cozy evenings, and guests can enjoy a large outdoor dining space with a view.
The Coachouse. - Chepstow
9.9 168 reviews

The Coachouse.

house
The Coachouse is a short distance from local landmarks and attractions in Monmouthshire, offering easy access to explore the region's beauty. Guests consistently rate the home excellent for its cleanliness, location, and overall experience.
The Coachouse has two bedrooms with en suite bathrooms and can accommodate up to four guests. This home features a full kitchen, dining area, and lounge, plus a downstairs toilet and cloakroom, ensuring a comfortable stay with all the necessities.

Best Chepstow houses with parking

Welsh Gatehouse: Historical Castle With Ev Charger - Chepstow
9.9 208 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.
Coppice Cabin - Private Hot Tub & Panoramic Views - Chepstow
10 76 reviews

Coppice Cabin - Private Hot Tub & Panoramic Views

cabin
Coppice Cabin is located in the Forest of Dean, close to the Wye Valley Area of Outstanding Natural Beauty and the River Severn. The cabin has excellent user, location, and cleanliness ratings.
This cozy woodland retreat can accommodate up to four guests in its one bedroom and one bathroom. Amenities include a wood-fired hot tub, a private garden, a well-equipped kitchen, and a comfortable living area with a wood-burning stove.
Orchard Holiday Cottage Is A Beautiful Romantic Dwelling Ideal For Couples. This Perfect Property Is - Chepstow
10 1 review

Orchard Holiday Cottage Is A Beautiful Romantic Dwelling Ideal For Couples. This Perfect Property Is

cottage, Chepstow
This pet-friendly Chepstow cottage, near Parva Farm Vineyard, the River Wye, and Tintern Abbey, offers convenient access to Chepstow's attractions.
The 108-square-foot (10 sq ft is incorrect, assuming it's 108 sq ft) one-bedroom, one-bathroom house sleeps two, features a fully equipped kitchen with a dishwasher, and includes a garden, parking, and Wi-Fi.
Severn Estuary Lodge. - Chepstow
9.5 4 reviews

Severn Estuary Lodge.

farm
This renovated lodge in Sedbury offers direct access to Offa's Dyke Path, with Chepstow Castle and Tintern Abbey a short drive away.
This farm accommodates up to 4 guests, featuring a kitchen with a fridge and freezer, 1 bathroom, and a garden, with ample parking on a pebble driveway.

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.

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.

Orchard Cottage Monmouthshire - Chepstow
10 1 review

Orchard Cottage Monmouthshire

house, Saint Arvans

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 Nook - Chepstow
10 1 review

The Nook

house, Tidenham
©2026 cozycozy.com