Holiday Rentals in Chepstow

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Chepstow holiday rentals
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Best Holiday rentals and Airbnb offers in Chepstow

Discover Central Holiday Rentals in Chepstow

Coordinate an unforgettable urban break using private, independent holiday rentals for couples situated close to vibrant Chepstow landmarks.

The Pink Cottage - Chepstow
9.7 76 reviews

The Pink Cottage

apartment
This recently refurbished fisherman's cottage in Chepstow, Monmouthshire, is a short walk (less than 1 km) from the River Wye and Chepstow Castle.
Sleeping up to eight guests, the three-bedroom property boasts a living room, dining room, kitchen with dishwasher, family bathroom, boot room, west-facing courtyard garden, parking, and Wi-Fi; its location offers easy access to Offa's Dyke Path and the Wales Coast Path.
Chepstow Apartmentshort Walk To Town&free Parking - Chepstow
10 45 reviews

Chepstow Apartmentshort Walk To Town&free Parking

apartment
This newly renovated one-bedroom flat is situated in a peaceful, upscale residential area of Chepstow, a 5-minute walk from the town centre and within easy reach of the Wye Valley Area of Outstanding Natural Beauty, with Chepstow Castle a short stroll away.
This accommodation offers a private entrance, a king-size bed, a 60-inch smart TV, and a fully equipped kitchen with a dishwasher, providing a comfortable base for exploring local walking trails, historical sites like Tintern Abbey (a short drive/walk), and prestigious golf courses such as St Pierre Golf Club (5 minutes away), while also being conveniently located for grocery shopping at Tesco and M&S Foodhall and travel via Chepstow Train Station.
Cromwell House, Central Chepstow - Chepstow
9.8 147 reviews

Cromwell House, Central Chepstow

apartment
This charming flat is situated in the heart of Chepstow, a historic town in Monmouthshire, just a short walk from Chepstow Castle. It's received excellent ratings for location, cleanliness and user experience.
The apartment has two double bedrooms, a spacious kitchen with dining space, and a bathroom with a bath and shower, comfortably accommodating up to four guests. It's fully equipped with everything you need for a comfortable stay, including Wi-Fi, and its recent refurbishment ensures a modern and clean environment.
Apartment 6 - Richmond House - Chepstow
9.5 55 reviews

Apartment 6 - Richmond House

apartment
This one-bedroom apartment in the Wye Valley, Monmouthshire, is situated just 16km from the historic Tintern Abbey and 10km from the town of Chepstow. The apartment is perfect for a couple seeking a peaceful retreat, with modern amenities and original Victorian features, including high ceilings and large sash windows.

Best Chepstow holiday rentals with air conditioning

Old Ferry View - Chepstow
9.5 220 reviews

Old Ferry View

apartment, Bristol
Old Ferry View is a peaceful apartment located in Bristol, about 9.3 miles from Bristol Parkway Station and 13 miles from Bristol Zoo, offering a tranquil escape from the city centre. It has received excellent ratings for its location, cleanliness, and overall user experience.
This one-bedroom flat, with a floor area of 10 square metres, can accommodate up to four guests. The apartment features a fully equipped kitchenette with a microwave, air conditioning, a private patio, complimentary Wi-Fi, parking, and a shuttle service for exploring the city and surrounding areas.

Frequently asked questions about holiday rentals in Chepstow

  • What are some interesting places to visit in or near Chepstow?

    Chepstow Castle is a must-see, a huge Norman fortress with a fascinating history. You can also visit the Tintern Abbey, a beautiful ruined abbey just outside Chepstow, and the National Trust property, The 18th-century Piercefield House and Gardens, with its stunning views across the Wye Valley.
  • What are the best Airbnb and holiday rentals in Chepstow?

    Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2 are among the best Airbnb and holiday rentals in Chepstow.

  • Which walking or cycling routes are the best in Chepstow?

    The Wye Valley Walk is a popular route that takes you through some of the most beautiful scenery in the area. For cyclists, the Forest of Dean is a great place to explore, with plenty of off-road trails.
  • What are the most popular Airbnbs in Chepstow?

    Among the Airbnbs in Chepstow, Chepstow Town - Welsh Cottage, Sedbury Farm Cottages #2 and Peaceful - Rural Apartment With River Views are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Chepstow?

    You can go kayaking or canoeing on the River Wye, play golf at the Chepstow Golf Club, or go horse riding in the surrounding countryside. There are also plenty of opportunities for fishing, hiking, and mountain biking.
  • What are the best holiday rentals with a pool in Chepstow?

  • What other towns or cities can be easily accessed from Chepstow?

    You can easily get to Bristol and Cardiff by car or train. The Forest of Dean is also just a short drive away.
  • What are the best rentals for families and kids in Chepstow?

    The best rentals for families and kids in Chepstow are Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2.

  • What amenities are commonly available in vacation rentals in Chepstow?

    Most vacation rentals in Chepstow offer Wi-Fi, parking, and bedding. Many also have kitchen facilities, washing machines, and TVs. Some may even have gardens or balconies.
  • What are the best rentals or Airbnbs with a jacuzzi in Chepstow?

    The best holiday rentals or Airbnb with a jacuzzi in Chepstow are 5 Bed Luxury House With Swimming Pool, 5br Luxury House With Swimming Pool Chepstow Town and Court Park Barn.

  • What time of year is best to rent a vacation rental Chepstow?

    The best time to visit Chepstow is during the spring or autumn, when the weather is mild and the crowds are smaller. Summer can be busy and hot, while winter can be cold and wet.

Popular destinations

Best Self-Catering Holiday Rentals with a Terrace in Chepstow

Choosing a holiday rental in Chepstow with a private balcony offers city skyline views that are worth every penny. Compare options and find yours.

South Wales Yurt-cosy, Log Burner & Private Garden - Chepstow
9.4 11 reviews

South Wales Yurt-cosy, Log Burner & Private Garden

glamping, Undy
South Wales Yurt-Cosy, a unique yurt in Undy, South Wales, is located 31km from Bristol Parkway Station and 32km from the University of South Wales Cardiff campus.
This 16 square metre dwelling offers one bedroom, one bathroom, sleeps three guests, and features a private garden with a log burner, barbecue, and designated picnic area.
Large Modern Home, Free Parking, Families And Contractors Welcome - Chepstow
8.4 12 reviews

Large Modern Home, Free Parking, Families And Contractors Welcome

house, Bristol
This spacious Bristol house is situated 4.3km from Bristol Parkway Station and 11km from Clifton, offering easy access to both the station and the Clifton Suspension Bridge.
The 95 square metre property sleeps up to 11 guests in three bedrooms, two bathrooms, and boasts free Wi-Fi, parking, a garden, and a fully equipped kitchen including a microwave and dishwasher.
Olli's Cottage-terrace & Jacuzzi Optional - Chepstow
9.8 102 reviews

Olli's Cottage-terrace & Jacuzzi Optional

house, Bristol
Olli's Cottage is conveniently located in Bristol, just a short distance from Bristol Parkway Station and Bristol Zoo. The property enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The cottage offers a comfortable and modern stay for two guests, with one bedroom and one bathroom in a 70 square metre space. The property boasts a private patio, free parking, a well-equipped kitchen, a walk-in shower, a flat-screen TV, and a swimming pool and jacuzzi for ultimate relaxation.
Sedbury Farm Cottages - Chepstow
No reviews

Sedbury Farm Cottages

apartment, Chepstow
Holiday rental listing. You will be based in Chepstow.
Facilities and services: a kitchen, a fridge and a garden. This apartment in Chepstow also has a terrace!

Explore Holiday Rentals for Families in Chepstow

Getting the holiday rental right makes all the difference for a family trip to Chepstow. Find city attractions within easy reach. Start comparing now.

Baker's Bun | Sleeps 7 | Parking & Garden - Chepstow
No reviews

Baker's Bun | Sleeps 7 | Parking & Garden

apartment, Bradley Stoke
This four-bedroom house is located in a peaceful residential area of Bradley Stoke, offering convenient access to Bristol city centre (a short drive away) and major business parks like Aztec West, with Cribbs Causeway and The Wave inland surf lake nearby.
This spacious family-friendly property comfortably accommodates up to seven guests, featuring a conservatory overlooking a garden with a pond, a fully equipped kitchen with a double oven and air-fryer, multiple bathrooms, and private parking.
Gated 4 Guests House Free Parking - Chepstow
9.1 52 reviews

Gated 4 Guests House Free Parking

house, Bristol
This 2-bedroom house is conveniently located in Bristol, just 5.1km from Bristol Parkway Station and 8km from Bristol Cathedral. You can easily explore the city centre and surrounding areas by public transport or car, with free parking available on site.
The 65 square metre house comfortably accommodates up to 6 guests and includes a fully equipped kitchen, 2 bathrooms with showers, a washing machine, and free Wi-Fi. You'll also find a flat-screen TV, towels and linen service for an extra fee, making it a comfortable and convenient base for your Bristol stay.
Oak Lodge 1 At Lindors Country House - Chepstow
No reviews

Oak Lodge 1 At Lindors Country House

house, Saint Briavels
Oak Lodge 1 is a lodge located in Saint Briavels, 1.9 kilometres from St Briavel's Castle and 5.9 kilometres from Puzzlewood.
This spacious lodge offers accommodation for up to 7 guests with 2 bedrooms, a kitchenette, a bathroom with both bath and shower, and a patio with garden views, all within a 65 square meter floor area, and provides free on-site parking and WiFi.
Country Cottage With Truly Amazing Views Over The River Wye Valley. Pet Friendly - Chepstow
9.8 241 reviews

Country Cottage With Truly Amazing Views Over The River Wye Valley. Pet Friendly

cottage, LLandogo
This charming cottage is located in Monmouth, just a short distance from the River Wye, Parva Farm Vineyard, and Tintern Abbey, offering a peaceful escape in a picturesque setting. It has received excellent reviews from previous guests, making it a popular choice for travellers to the area.
This two-bedroom property can accommodate up to four guests, making it ideal for families or small groups. It features a fully equipped kitchen, a comfortable living area, and a private garden with a barbecue, perfect for enjoying the outdoors.

Choose the Right Self-Catering Holiday Rentals with Free Parking in Chepstow

Free on-site parking comes with these holiday rentals in Chepstow, allowing you to focus on the city centre from day one.

Tawny Cottage - Chepstow
No reviews

Tawny Cottage

house, Usk
Spacious Chepstow Home With Private Garden & Patio - Chepstow
9.9 98 reviews

Spacious Chepstow Home With Private Garden & Patio

apartment
The Elements Residence - Chepstow
No reviews

The Elements Residence

apartment, Chepstow
Top Lodge - Chepstow
10 2 reviews

Top Lodge

apartment

Check Out 5-Star Self-Catering Holiday Rentals in Chepstow

There is much to be said for a well-chosen luxury holiday rental or Airbnb in Chepstow. Discover wonderful rooms and locations worth the trip. Start comparing now.

The Willow - Studio 22 - Chepstow
No reviews

The Willow - Studio 22

studio, Patchway

Popular Pet-Friendly Holiday Rentals in Chepstow

Bringing your dog to Chepstow? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.

Luxury 4 Bed Former Hay Loft Sleeps 6 - Chepstow
10 1 review

Luxury 4 Bed Former Hay Loft Sleeps 6

house, Usk
Relax, Log Fires Hot Tub & Foreshore Dog Walks! - Chepstow
9.9 79 reviews

Relax, Log Fires Hot Tub & Foreshore Dog Walks!

apartment
Six Person Glamping Tent - Chepstow
8.9 85 reviews

Six Person Glamping Tent

glamping
Harthill Grange Bunkhouse - Unique 1850's Rural Country Accommodation - Chepstow
9.9 80 reviews

Harthill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

apartment, Lydney

Compare Holiday Rentals with a Pool in Chepstow

Pool access at your holiday rental makes a proper swim in the heart of the city part of your daily routine in Chepstow.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chepstow
9.7 14 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
Bilsham Meadows - Chepstow
9.6 21 reviews

Bilsham Meadows

house, Bristol

Guest-Favourite Holiday Rentals with a Hot Tub in Chepstow

Private hot tub access after a day in the city is one of those details that makes a trip to Chepstow truly memorable.

Top Lodge, Pet Friendly, Character Holiday Cottage In Penhow - Chepstow
No reviews

Top Lodge, Pet Friendly, Character Holiday Cottage In Penhow

apartment, Cas-Gwent
Peaceful Retreat With Hot Tub - Chepstow
9.2 84 reviews

Peaceful Retreat With Hot Tub

apartment
Foxholes Barn - Chepstow
9.6 39 reviews

Foxholes Barn

bungalow
Olli's Cottage-terrace &Jacuzzi - Chepstow
9.9 194 reviews

Olli's Cottage-terrace &Jacuzzi

apartment
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