Holiday Rentals Chepstow from £57: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Chepstow holiday rentals

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

1. The Honey Pot

Chepstow

includes taxes & fees

17 Sept - 18 Sept

A living room with two green sofas, a wooden coffee table, and a TV on a stand.

2. The Elements Residence

Chepstow

includes taxes & fees

3 Sept - 4 Sept

A bedroom with a bed, a window with curtains, a view of greenery, and a balcony with a railing.

3. Ferryman's Lodge

Chepstow

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

4. Top Lodge

Caerwent

includes taxes & fees

14 Sept - 15 Sept

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

5. The Snug

Caerwent

includes taxes & fees

4 Sept - 5 Sept

A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

6. Bottom Lodge

Caerwent

includes taxes & fees

9 Sept - 10 Sept

A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

7. The Priory Cellars Abbots Leigh

Bristol

Le-Anne

includes taxes & fees

1 Sept - 2 Sept

A living room with a black sofa, a glass coffee table, and a fireplace.

8. Your Stay Bristol Orchard Gate

Bristol

claire

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

9. Beautiful 1-bed Cottage in Trellech

Trellech United

Eva

includes taxes & fees

8 Sept - 9 Sept

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

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

Lydney

Samuel P.

includes taxes & fees

2 Sept - 3 Sept

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

Alvington

Philip R.

includes taxes & fees

2 Sept - 3 Sept

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.

12. Bilsham Meadows

Bristol

includes taxes & fees

7 Sept - 8 Sept

A conservatory with stone arches, potted plants, and a bench.

13. The Orangery Apartment

Bristol

Patricia

includes taxes & fees

1 Sept - 2 Sept

A cozy living room with two grey sofas, a wooden coffee table, and a dining area with wooden chairs and a table.

14. Cider Press Barn - UK12379

Lydney

John Littlewood

includes taxes & fees

12 Sept - 13 Sept

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

15. Bright & Beautiful Studio Flat in Bristol

Bristol

Katarina

A living room with a sofa, coffee table, TV, and a fruit bowl.

16. PREMIER SUITES Bristol Redcliffe

Bristol Floating Harbour

Gareth

includes taxes & fees

4 Sept - 5 Sept

A multi-story building with a stone facade, large windows, and a corner entrance.

17. Your Apartment - Pembroke House

Clifton

Harriet

includes taxes & fees

18 Sept - 19 Sept

A formal garden with a gravel path leading to a building with classical architecture.

18. Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath

Dyrham

Steven L.

includes taxes & fees

7 Sept - 8 Sept

A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

19. Lovely 1-bed Loft in Newport

Caerleon

JAYNE

includes taxes & fees

2 Sept - 3 Sept

20. The Cranbrook - Stylish Bristol Stay - 8 Guests

Bishopston

includes taxes & fees

6 Sept - 7 Sept

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Top Chepstow Hotel Reviews

Clayton Hotel Bristol City

10/10 Excellent

"Lovely location . Great stay !"

The Manor House At Celtic Manor

8/10 Good

"We had a really enjoyable stay at Celtic Manor. I slept incredibly well, the spa was excellent, and breakfast was a real highlight — very good quality with a fantastic choice. A £7 for a bowl of chips, expectations are naturally rather high. Sadly, these were more limp than luxurious — lacking the crispness and heat the price rather suggested. The bedroom itself was comfortable and nicely presented, although I do think the hotel needs to keep an eye on the rooms as they age. For a hotel of this standard, small signs of wear can quickly detract from the overall experience if they are not kept on top of. Overall, though, we had a lovely stay. The spa, a great night's sleep and an excellent breakfast were definite highlights."

Village Hotel Bristol

8/10 Good

"Bed was comfy, room was clean and tidy. Parking was easy Starbucks and pub good too. We did use the pool and gym which was clean and maintained. Only downside we found was after we came back from Bristol city centre which was just after 11pm as the bar was closed there was no where you could get water or even a bag of crisps so maybe a vending machine would be beneficial . No shops within walking distance. Apart from that excellent stay"

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 £57 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?

Beautifully converted stone barn with amazing views towards the black mountains : This holiday home rental outside of Chepstow is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Chepstow?

Choose from 13 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 Honey Pot

2. The Elements Residence

3. Ferryman's Lodge

4. Top Lodge

5. The Snug

6. Bottom Lodge

7. The Priory Cellars Abbots Leigh

8. Your Stay Bristol Orchard Gate

9. Beautiful 1-bed Cottage in Trellech

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

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

12. Bilsham Meadows

13. The Orangery Apartment

14. Cider Press Barn - UK12379

15. Bright & Beautiful Studio Flat in Bristol

16. PREMIER SUITES Bristol Redcliffe

17. Your Apartment - Pembroke House

18. Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath

19. Lovely 1-bed Loft in Newport

20. The Cranbrook - Stylish Bristol Stay - 8 Guests

Find holiday rentals that suit your style

Top Chepstow Hotel Reviews

Clayton Hotel Bristol City

Find out more about Chepstow

Explore a world of travel with Expedia

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