The ruins of a large, historic stone building with multiple arches and a tall, narrow tower.

Chepstow Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chepstow vacation rentals

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

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is ₩699,575
₩839,490 total
includes taxes & fees
Oct 17 - Oct 18
The Honey Pot
A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

2. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
Bottom Lodge
A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

3. The Snug

The Snug
3.0 star property
Caerwent
The price is ₩434,219
₩521,063 total
includes taxes & fees
Oct 23 - Oct 24
The Snug
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

4. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is ₩606,097
₩727,316 total
includes taxes & fees
Oct 18 - Oct 19
Top Lodge
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.

5. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is ₩2,145,463
₩2,574,556 total
includes taxes & fees
Oct 19 - Oct 20
Bilsham Meadows
A stone wall entrance to a building with a black door and a small trash bin.

6. Beautiful 1-bed Cottage in Trellech

Beautiful 1-bed Cottage in Trellech
3.0 star property
Trellech United
9.2 out of 10, Wonderful, (25 reviews)
"Lovely staff and great space to relax."
United Kingdom
Eva
The price is ₩160,562
₩160,562 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful 1-bed Cottage in Trellech
A living room with a sofa, coffee table, TV, and a fruit bowl.

7. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (194 reviews)
"Great flat Stayed for o e night so only used for the night Well equipped"
United Kingdom
rasiah
The price is ₩131,560
₩157,865 total
includes taxes & fees
Oct 18 - Oct 19
PREMIER SUITES Bristol Redcliffe
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.

8. Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.4 out of 10, Very good, (158 reviews)
"Fast and easy check-in, helpful staff and quick production of a VAT invoice for expenses. The apartment was clean, roomy and comfortable, with a good bed, large TV, well equipped kitchen and great shower too. Parking is very convenient and placed at the back of the building in the multi-storey car park. Local supermarket very close too. Great."
United Kingdom
Andrew
The price is ₩113,743
₩136,491 total
includes taxes & fees
Oct 13 - Oct 14
Quay Apartments Clarence House
A two-story brick building with a black door and windows, parked cars in front, and trees with green leaves.

9. Your Stay Bristol Beaufort House

Your Stay Bristol Beaufort House
4.0 star property
Clifton
9.8 out of 10, Exceptional, (36 reviews)
"Gorgeous apartment beautifully set out - loved it - parking good - would recommend"
United Kingdom
Amy
The price is ₩279,369
₩335,243 total
includes taxes & fees
Oct 13 - Oct 14
Your Stay Bristol Beaufort House
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

10. Frederick Place Your Apartment

Frederick Place Your Apartment
4.5 star property
Clifton
7.4 out of 10, Good, (12 reviews)
"Beautiful, spacious apartment in a fantastic location, cant recommend enough"
United Kingdom
Roger
The price is ₩303,019
₩363,623 total
includes taxes & fees
Oct 23 - Oct 24
Frederick Place Your Apartment
A conservatory with stone arches, potted plants, and a bench.

11. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (81 reviews)
"Wonderful property and hosts. Great parking and facilities in property with plenty of space and stocked kitchen facilities. Would stay again"
United Kingdom
Janet
The price is ₩141,902
₩141,902 total
includes taxes & fees
Oct 14 - Oct 15
The Orangery Apartment
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

12. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (144 reviews)
"Nice place to stay for a few nights and very well equipped"
United Kingdom
John
The price is ₩134,807
₩134,807 total
includes taxes & fees
Nov 1 - Nov 2
The Priory Cellars Abbots Leigh
A modern living room with a large window, a sofa, a coffee table, and a TV mounted on the wall.

13. Waterside Living I Luxe Apartments

Waterside Living I Luxe Apartments
4.0 star property
Bristol Floating Harbour
9.4 out of 10, Exceptional, (3 reviews)
"Very spacious and clean with an outside patio with a great view of the busy harbour. Lots of shops/bars restaurants and activities for all ages in walking distance."
United Kingdom
Tina
The price is ₩307,447
₩368,937 total
includes taxes & fees
Oct 23 - Oct 24
Waterside Living I Luxe Apartments
A spacious living room with a large sofa set, a wooden coffee table, and a television. There is a large sliding glass door leading to a patio with a view of the outdoors.

14. Hidden Well

Hidden Well
2.5 star property
Bristol
The price is ₩1,953,984
₩2,344,781 total
includes taxes & fees
Oct 19 - Oct 20
Hidden Well
A compact kitchen with a microwave, toaster, and coffee maker. A bed with a headboard is visible in the background.

15. Hotwells Your Apartment

Hotwells Your Apartment
3.0 star property
Clifton
7.4 out of 10, Good, (11 reviews)
"Small clean room cosy and warm bus stop right outside the apartments but very noisy you can hear every move of other residents in the property"
Ireland
Hoa Minh
The price is ₩172,942
₩207,530 total
includes taxes & fees
Oct 13 - Oct 14
Hotwells Your Apartment
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

16. 1 Bed Loft - Sleeps 2 - Parking - Wifi

1 Bed Loft - Sleeps 2 - Parking - Wifi
3.0 star property
Caerleon
8.6 out of 10, Excellent, (7 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is ₩125,938
₩151,125 total
includes taxes & fees
Oct 14 - Oct 15
1 Bed Loft - Sleeps 2 - Parking - Wifi
A modern kitchen with wooden cabinets, a dining table with chairs, and large windows with curtains.

17. PREMIER SUITES PLUS Bristol Cabot Circus

PREMIER SUITES PLUS Bristol Cabot Circus
4.0 star property
Bristol City Centre
8.6 out of 10, Excellent, (220 reviews)
"Great location next to the shops and 1 min to some restaurants, or ten mins walk to the bars and restaurants by the river. Apartment was amazing. Two bedrooms, two bathrooms. Kitchen with microwave. Clean and very spacious."
United Kingdom
GILLIAN
The price is ₩131,560
₩157,865 total
includes taxes & fees
Oct 18 - Oct 19
PREMIER SUITES PLUS Bristol Cabot Circus
A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

18. Higgihaus 26 Clare Street Aparthotel

Higgihaus 26 Clare Street Aparthotel
3.5 star property
Bristol City Centre
8.0 out of 10, Very good, (5 reviews)
"Lovwly property rught in the thick of it!"
United Kingdom
Tracey
The price is ₩174,272
₩285,753 total
includes taxes & fees
Oct 18 - Oct 19
Higgihaus 26 Clare Street Aparthotel
A modern bedroom with a large bed, a bedside table with a lamp, and a view of the city through a window.

19. Colston Street - Your Apartment

Colston Street - Your Apartment
3.0 star property
Bristol
8.8 out of 10, Excellent, (8 reviews)
"I enjoyed it highly recommended.....will do it anytime again.....perfect for a get away peace quiet an great....."
United Kingdom
Sansha
The price is ₩199,549
₩239,459 total
includes taxes & fees
Oct 14 - Oct 15
Colston Street - Your Apartment
A multi-story building with a stone facade, large windows, and a corner entrance.

20. Your Apartment - Pembroke House

Your Apartment - Pembroke House
4.0 star property
Clifton
8.4 out of 10, Very good, (7 reviews)
"Great location in Clifton. Combination washer and dryer worked well. Kitchen was well equipped. Bedroom was in need of a vacuum and mattress was a bit soft for our liking."
Canada
Michele
The price is ₩218,179
₩261,815 total
includes taxes & fees
Nov 6 - Nov 7
Your Apartment - Pembroke House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chepstow Hotel Reviews

Clayton Hotel Bristol City

Clayton Hotel Bristol City

8/10 Good
"Lovely hotel, very comfy room. Great location. Very impressed. Thank you for a great stay"
Jane 1-night trip
Posted less than an hour ago
Clayton Hotel Bristol City

Find out more about Chepstow

Search for Vacation rentals in Chepstow on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chepstow using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chepstow!

Frequently asked questions

Can I find a vacation rental in Chepstow?

Yes, there are vacation rentals in Chepstow close to Chepstow Leisure Centre, or you can choose a secluded option if you'd like a relaxing place to 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 vacation home rentals in Chepstow?

6 Bed House Sleeps 13 - Private Garden: Located near Chepstow, this vacation home rental 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 you can cook with friends or family.

How many vacation rentals are there in Chepstow?

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

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 vacation rental in Chepstow like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Chepstow. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.