Chepstow Holiday Rentals from AU$87: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Chepstow has to offer?

6 Bed House Sleeps 13 - Private Garden : This holiday home rental outside of Chepstow is equipped with a garden, laundry facilities and free WiFi to help you feel comfortable during your stay. It has 6 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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Our top choices for Chepstow holiday rentals

A modern kitchen with white cabinetry, a built-in oven, and a dining area with a wooden table and chairs.

1. New 3 Bedroom Apartment Next to Station

Chepstow

includes taxes & fees

26 Nov - 27 Nov

A modern kitchen with a built-in oven and a dining area with a table and chairs.

2. The Long Weekend

Chepstow

includes taxes & fees

15 Nov - 16 Nov

A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

3. The Honey Pot

Chepstow

includes taxes & fees

14 Nov - 15 Nov

A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

4. The Snug

Caerwent

includes taxes & fees

19 Nov - 20 Nov

An outdoor patio with a table and chairs, a large umbrella, a hot tub, and a wooden building in the background.

5. Bottom Lodge

Caerwent

includes taxes & fees

21 Nov - 22 Nov

A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

6. Top Lodge

Caerwent

includes taxes & fees

14 Nov - 15 Nov

A stone wall entrance to a building with a black door and a small trash bin.

7. Beautiful 1-bed Cottage in Trellech

Trellech United

Eva

includes taxes & fees

22 Nov - 23 Nov

A historic stone bridge with a moat, surrounded by modern buildings and a railway track.

8. Livin' Serviced Apartments - Newport

St Julians

Lucy

includes taxes & fees

19 Nov - 20 Nov

9. A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

Alvington

Philip R.

includes taxes & fees

16 Nov - 17 Nov

A spacious loft-style living area with a large wooden dining table, multiple seating options, and a large sliding glass door leading to a balcony.

10. Bilsham Meadows

Bristol

includes taxes & fees

2 Dec - 3 Dec

A historic building with a stone facade, large windows, and a gated entrance.

11. The Priory Cellars Abbots Leigh

Bristol

John

includes taxes & fees

16 Nov - 17 Nov

A hanging pendant light with a ribbed design.

12. 526 Gloucester Flat 1 - Hopewell

Horfield

Vanessa

includes taxes & fees

6 Dec - 7 Dec

A neatly made bed with pillows and folded towels, a wooden dresser, a window with curtains, and a view of the outside.

13. Your Stay Bristol Orchard Gate

Bristol

claire

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a sofa, a flat-screen TV, and a sliding glass door leading to an outdoor area.

14. Stylish Marina Apartment with Stunning Views

Portishead

Carol D.

includes taxes & fees

11 Nov - 12 Nov

A historic building with a classical facade, large windows, and a corner entrance.

15. Belvilla Newport City Centre Hotel - Deluxe Double Room

Newport City Centre

Anonymous traveller

includes taxes & fees

22 Nov - 23 Nov

A row of traditional terraced houses with a narrow street in front.

16. Bright & Beautiful Studio Flat in Bristol

Bristol

Katarina

includes taxes & fees

11 Nov - 12 Nov

17. The Orangery Apartment

Bristol

Narelle

includes taxes & fees

12 Nov - 13 Nov

An open wooden door leading to a stone courtyard with a stone building in the background.

18. 2 bedroom accommodation in Lydney

Lydney

Lorraine Galea

includes taxes & fees

26 Nov - 27 Nov

A gravel driveway leading to a stone wall and a building with ivy-covered walls.

19. HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

Lydney

Samuel P.

includes taxes & fees

16 Nov - 17 Nov

A stone house with a sloped roof, a wooden gate, and a stone wall.

20. The Pound

Trellech United

Kevin

includes taxes & fees

20 Nov - 21 Nov

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Find holiday rentals that suit your style

Top Chepstow Hotel Reviews

A large castle with multiple towers and a well-maintained garden.

Thornbury Castle, Relais & Châteaux

Bristol

10/10 Excellent

helga

A cozy living room with a sofa, coffee table, and a lamp. There is a window with curtains, a door, and a mirror on the wall.

The Bell Inn

Stroud

10/10 Excellent

Mark

A modern building with a checkered patio area, outdoor seating, and potted plants.

Mollie's Bristol

Bristol

10/10 Excellent

Karen

A hotel room with two beds, a headboard with a light fixture, a bedside table, a wall-mounted picture, and a window with curtains.

Two Rivers, Chepstow by Marston’s Inns

Chepstow

10/10 Excellent

Stuart

A hotel room with a wooden headboard, two patterned pillows, a bed with white linens, and a view of a lake through a window.

Charlcombe Inn

Lansdown

10/10 Excellent

A lovely stay just outside Bath The hotel looks stunning from the outside, especially in the evening when the façade and grounds are beautifully lit up. A real plus is the layout: the guest rooms are situated in a separate building away from the main bar and dining area, which meant our stay was peaceful and free from pub noise. Our room was surprisingly spacious, bright, and well equipped with all the essentials for a comfortable visit. The location worked out brilliantly for us as well....

Igor

A room with a green brick wall, a wooden bench, a chair, a small table, and a shelf with books and a pineapple.

Hotel Indigo Cardiff by IHG

Cardiff City Centre

10/10 Excellent

Shiann

The Priory Cellars Abbots Leigh

Bristol

10/10 Excellent

Laura

A modern lounge area with sofas, chairs, and a table, featuring a flat-screen TV mounted on the wall.

Holiday Inn Express Newport by IHG

Coedkernew

10/10 Excellent

Miro

Find out more about Chepstow

Everything you need to know about Chepstow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chepstow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chepstow holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Chepstow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chepstow. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chepstow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chepstow holiday rentals we have selected for you start as low as AU$87 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chepstow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chepstow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chepstow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Chepstow?

Yes, there are holiday rentals in Chepstow close to Chepstow Leisure Centre, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and spas in Chepstow. Allow lots of time to check out the riverfront and bars during your visit.

What are some of the best holiday rentals that Chepstow has to offer?

6 Bed House Sleeps 13 - Private Garden: This holiday home rental outside of Chepstow is equipped with a garden, laundry facilities and free WiFi to help you feel comfortable during your stay. It has 6 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chepstow?

Choose from 14 Expedia holiday rentals in Chepstow for a memorable holiday.

What’s there to see and do in Chepstow?

Wye Valley and River Wye are a couple of scenic spots to enjoy the outdoors, whereas Chepstow Museum is one of the cultural attractions. Chepstow Racecourse and St. Pierre Country Club are other places to visit while you're in town.

What’s a holiday rental in Chepstow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chepstow. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for small groups.

Chepstow Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chepstow holiday rentals

1. New 3 Bedroom Apartment Next to Station

2. The Long Weekend

3. The Honey Pot

4. The Snug

5. Bottom Lodge

6. Top Lodge

7. Beautiful 1-bed Cottage in Trellech

8. Livin' Serviced Apartments - Newport

9. A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

10. Bilsham Meadows

11. The Priory Cellars Abbots Leigh

12. 526 Gloucester Flat 1 - Hopewell

13. Your Stay Bristol Orchard Gate

14. Stylish Marina Apartment with Stunning Views

15. Belvilla Newport City Centre Hotel - Deluxe Double Room

16. Bright & Beautiful Studio Flat in Bristol

17. The Orangery Apartment

18. 2 bedroom accommodation in Lydney

19. HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

20. The Pound

Find holiday rentals that suit your style

Top Chepstow Hotel Reviews

Thornbury Castle, Relais & Châteaux

10/10 Excellent

Find out more about Chepstow

Chepstow holiday rentals: An excellent choice for every season

How to find incredible deals on Chepstow rentals

Frequently Asked Questions

Can I find a holiday rental in Chepstow?

What are some of the best holiday rentals that Chepstow has to offer?

How many holiday rentals are there in Chepstow?

What’s there to see and do in Chepstow?

What’s a holiday rental in Chepstow like?