Holiday Rentals Chepstow from £69: Find Short-Term Rentals & Holiday Accommodations

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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In two weeks

In two months

In three months

In four months

Our top choices for Chepstow holiday rentals

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

1. The Long Weekend

Chepstow

includes taxes & fees

9 Nov - 10 Nov

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

2. The Snug

Caerwent

includes taxes & fees

20 Nov - 21 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 living room with a sofa, armchair, coffee table, and a painting of red buses.

4. Bottom Lodge

Caerwent

includes taxes & fees

8 Nov - 9 Nov

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

5. Top Lodge

Caerwent

includes taxes & fees

3 Nov - 4 Nov

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

Alvington

Philip R.

includes taxes & fees

1 Nov - 2 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

1 Nov - 2 Nov

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

8. Livin' Serviced Apartments - Newport

St Julians

Donald

includes taxes & fees

30 Oct - 31 Oct

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.

9. Bilsham Meadows

Bristol

includes taxes & fees

9 Nov - 10 Nov

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

10. The Priory Cellars Abbots Leigh

Bristol

John

includes taxes & fees

1 Nov - 2 Nov

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

11. Stylish Marina Apartment with Stunning Views

Portishead

Ruth S.

includes taxes & fees

1 Nov - 2 Nov

12. The Orangery Apartment

Bristol

Janet

includes taxes & fees

1 Nov - 2 Nov

A modern building with a brick facade and large windows.

13. PREMIER SUITES PLUS Bristol Cabot Circus

Bristol City Centre

GILLIAN

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a built-in oven, a dining area with a round table and chairs, and large windows with a view of a bridge.

14. Quay Apartments Clarence House

St Julians

Andrew

includes taxes & fees

29 Nov - 30 Nov

A bedroom with a sloped ceiling, a bed with blue bedding, a window with curtains, and a decorative light fixture.

15. Old Fleece Apartments

Stroud

Charlotte

includes taxes & fees

15 Nov - 16 Nov

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

16. 2 bedroom accommodation in Lydney

Lydney

Lorraine Galea

includes taxes & fees

2 Nov - 3 Nov

A cozy interior with a stone wall, wooden beams, a seating area with cushions, and a table with a menu.

17. 1 Bed Loft - Sleeps 2 - Parking - Wifi

Caerleon

JAYNE

includes taxes & fees

30 Oct - 31 Oct

A modern living room with a sofa, a glass coffee table, a TV, and a view of the city through large windows.

18. Cleyro Serviced Apartments-Finzels Reach

Bristol Floating Harbour

Alexander

A cozy room with a bed, a small table, a sofa, and a view of the outdoors.

19. The Coach House and The Stable

Stroud

Tania

includes taxes & fees

8 Nov - 9 Nov

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

20. The Pound

Trellech United

Kevin

includes taxes & fees

8 Nov - 9 Nov

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Top Chepstow Hotel Reviews

Leonardo Royal Hotel Bristol - formerly The Bristol Hotel

10/10 Excellent

"Very comfy bed and a great nights sleep. Parking great and very reasonable. Close to everything. Breakfast was delicious and very good value for money at £18 pp"

The Coach & Horses Hotel

8/10 Good

"I stayed for one night on a work trip, so spent very little time in the hotel. I arrived at around 8:30pm, the person on reception was friendly and welcoming, the room was clean and the bed was comfortable, and it was a good price. I left at 8am the following morning and didn't have time for breakfast. I would stay there again as I was happy with the facilities, which met my needs perfectly."

De Vere Tortworth Court

8/10 Good

"The hotel is beautiful, lovely places to have drinks and eat, the garden were beautiful in the morning and it was pleasant to sit outside on an autumn morning... most staff very helpful and willing. Areas requiring improvement: it was a busy evening and the main restaurant was booked out, then again at breakfast it was full, we got informed we could sit in the connecting library (which didn't have proper tables for eating) or the atrium so twice on our stay we didn't get to eat in the main restaurant. We paid for a suite and it didn't have water in the rooms, on asking I got told about water filters on each floor which is great environmentally but actually having had no bottles provided in the room for obtaining water just made the concept a bit useless! Also on asking for potentially an extra half hour in the morning I got told I could if I paid more money yet I had purchased a suite and actually this should be a perk occasionally especially if you have young children. A few niggles that take away from what could be a great hotel get away."

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, apart-hotels, 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 favorite 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 depends 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 £69 per night. Entering your travel dates in the search wizard you might find 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.

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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.

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Check prices for these dates

Our top choices for Chepstow holiday rentals

1. The Long Weekend

2. The Snug

3. The Honey Pot

4. Bottom Lodge

5. Top Lodge

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

7. Beautiful 1-bed Cottage in Trellech

8. Livin' Serviced Apartments - Newport

9. Bilsham Meadows

10. The Priory Cellars Abbots Leigh

11. Stylish Marina Apartment with Stunning Views

12. The Orangery Apartment

13. PREMIER SUITES PLUS Bristol Cabot Circus

14. Quay Apartments Clarence House

15. Old Fleece Apartments

16. 2 bedroom accommodation in Lydney

17. 1 Bed Loft - Sleeps 2 - Parking - Wifi

18. Cleyro Serviced Apartments-Finzels Reach

19. The Coach House and The Stable

20. The Pound

Find holiday rentals that suit your style

Top Chepstow Hotel Reviews

Leonardo Royal Hotel Bristol - formerly The Bristol Hotel

Find out more about Chepstow

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