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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$527 nightly
The price is $633
Nov 13 - Nov 14
Total with taxes and fees
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
$457 nightly
The price is $548
Nov 2 - Nov 3
Total with taxes and fees
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
$327 nightly
The price is $393
Oct 25 - Oct 26
Total with taxes and fees
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
$457 nightly
The price is $548
Oct 27 - Oct 28
Total with taxes and fees
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
$1,617 nightly
The price is $1,941
Nov 1 - Nov 2
Total with taxes and fees
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
$109 nightly
The price is $109
Oct 25 - Oct 26
Total with taxes and fees
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
$99 nightly
The price is $119
Oct 25 - Oct 26
Total with taxes and fees
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
$76 nightly
The price is $91
Oct 22 - Oct 23
Total with taxes and fees
Quay Apartments Clarence House
A conservatory with stone arches, potted plants, and a bench.

9. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (82 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
$107 nightly
The price is $107
Oct 22 - Oct 23
Total with taxes and fees
The Orangery Apartment
A two-story brick building with a black door and windows, parked cars in front, and trees with green leaves.

10. 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
$206 nightly
The price is $247
Oct 22 - Oct 23
Total with taxes and fees
Your Stay Bristol Beaufort House
A modern kitchen with white cabinets, a built-in oven, and a stainless steel range hood.

11. Your Apartment Clifton House

Your Apartment Clifton House
3.0 star property
Bristol
7.4 out of 10, Good, (117 reviews)
"Excellent room and great location Online check I wasn't the easiest but no issues once I arrived. Really nice property for the price"
United Kingdom
Freddie
$129 nightly
The price is $155
Oct 22 - Oct 23
Total with taxes and fees
Your Apartment Clifton House
A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

12. 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
$165 nightly
The price is $198
Oct 22 - Oct 23
Total with taxes and fees
Higgihaus 26 Clare Street Aparthotel
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

13. 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
$165 nightly
The price is $198
Oct 23 - Oct 24
Total with taxes and fees
Frederick Place Your Apartment
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

14. 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
$102 nightly
The price is $102
Nov 1 - Nov 2
Total with taxes and fees
The Priory Cellars Abbots Leigh
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.

15. Hidden Well

Hidden Well
2.5 star property
Bristol
$1,473 nightly
The price is $1,768
Oct 28 - Oct 29
Total with taxes and fees
Hidden Well
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
$95 nightly
The price is $114
Oct 24 - Oct 25
Total with taxes and fees
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, (221 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
$89 nightly
The price is $107
Oct 25 - Oct 26
Total with taxes and fees
PREMIER SUITES PLUS Bristol Cabot Circus
A modern bedroom with a large bed, a bedside table with a lamp, and a view of the city through a window.

18. Colston Street - Your Apartment

Colston Street - Your Apartment
3.0 star property
Bristol
8.4 out of 10, Very good, (10 reviews)
"I enjoyed it highly recommended.....will do it anytime again.....perfect for a get away peace quiet an great....."
United Kingdom
Sansha
$146 nightly
The price is $175
Nov 13 - Nov 14
Total with taxes and fees
Colston Street - Your Apartment
A modern living room with a large window, a sofa, a coffee table, and a TV mounted on the wall.

19. 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
$211 nightly
The price is $254
Nov 6 - Nov 7
Total with taxes and fees
Waterside Living I Luxe Apartments
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
$137 nightly
The price is $164
Oct 23 - Oct 24
Total with taxes and fees
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

Moxy Bristol

Moxy Bristol

8/10 Good
"Stayed for one night on my own. Close to Cabot circus shopping and easy to get to from temple meads station. My room was very clean and comfortable. A pleasant stay."
Jennifer 1-night trip
Posted 1 hour ago
Moxy Bristol

Find out more about Chepstow

Everything you need to know about Chepstow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chepstow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chepstow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chepstow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $91 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.