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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$521 nightly
The price is $626
Sep 29 - Sep 30
Total with taxes and fees
The Honey Pot
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

2. Top Lodge

Top Lodge
2.0 star property
Caerwent
$452 nightly
The price is $542
Oct 2 - Oct 3
Total with taxes and fees
Top Lodge
A covered outdoor seating area with a pergola, wooden benches, and a table with a bottle and glasses.

3. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
$377 nightly
The price is $452
Oct 8 - Oct 9
Total with taxes and fees
Ferryman's Lodge
A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

4. The Snug

The Snug
3.0 star property
Caerwent
$324 nightly
The price is $388
Oct 13 - Oct 14
Total with taxes and fees
The Snug
A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

5. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
$452 nightly
The price is $542
Oct 11 - Oct 12
Total with taxes and fees
Bottom 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.

6. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
$1,599 nightly
The price is $1,918
Sep 29 - Sep 30
Total with taxes and fees
Bilsham Meadows
A wooden, arched, single-room cabin with two beds and two chairs, surrounded by grass and trees.

7. Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (26 reviews)
"Brilliant holiday camp, very friendly staff, beautiful location, idea for familys ans couples."
United Kingdom
Tina
$58 nightly
The price is $70
Oct 7 - Oct 8
Total with taxes and fees
Broadstone Park Camping & Fishery
A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

8. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (142 reviews)
"Nice place to stay for a few nights and very well equipped"
United Kingdom
John
$100 nightly
The price is $100
Sep 27 - Sep 28
Total with taxes and fees
The Priory Cellars Abbots Leigh
A stone wall entrance to a building with a black door and a small trash bin.

9. 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
$115 nightly
The price is $115
Oct 4 - Oct 5
Total with taxes and fees
Beautiful 1-bed Cottage in Trellech
A spacious lobby with a large sofa, patterned chairs, a wooden coffee table, and a large window offering a view of the street.

10. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
$197 nightly
The price is $236
Sep 29 - Sep 30
Total with taxes and fees
Orchard by UTDM
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)
"Lovely clean, spacious, well-equipped apartment in a beautiful building. The accommodation has everything you need for a short or long stay. Hosts were very welcoming and helpful. There are lovely walks in the surrounding area and it is also very convenient for getting into Bristol."
United States
Patricia
$106 nightly
The price is $106
Sep 28 - Sep 29
Total with taxes and fees
The Orangery Apartment
A modern kitchen with built-in appliances, a dining area with a table and chairs, and a living space with a sofa and coffee table.

12. The Sixty 19 Stylish Studios and Apt.

The Sixty 19 Stylish Studios and Apt.
3.0 star property
Adamsdown
$116 nightly
The price is $139
Oct 11 - Oct 12
Total with taxes and fees
The Sixty 19 Stylish Studios and Apt.
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.

13. 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 $92
Oct 26 - Oct 27
Total with taxes and fees
Quay Apartments Clarence 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.

14. 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
$154 nightly
The price is $185
Sep 28 - Sep 29
Total with taxes and fees
Higgihaus 26 Clare Street Aparthotel
A living room with a sofa, coffee table, TV, and a fruit bowl.

15. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (193 reviews)
"Great flat Stayed for o e night so only used for the night Well equipped"
United Kingdom
rasiah
$98 nightly
The price is $118
Sep 27 - Sep 28
Total with taxes and fees
PREMIER SUITES Bristol Redcliffe
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.

16. Hidden Well

Hidden Well
2.5 star property
Bristol
$1,456 nightly
The price is $1,747
Sep 29 - Sep 30
Total with taxes and fees
Hidden Well
A bedroom with a bed, bedside table, lamp, artwork, curtains, and a radiator.

17. Your Stay Bristol Hamilton Court

Your Stay Bristol Hamilton Court
4.0 star property
Stokes Croft
9.0 out of 10, Wonderful, (112 reviews)
"Place is convenient, comfortable and safe"
Singapore
Tan
$188 nightly
The price is $226
Sep 27 - Sep 28
Total with taxes and fees
Your Stay Bristol Hamilton Court
A cozy room with a bed, a small table, a sofa, and a view of the outdoors.

18. The Coach House and The Stable

The Coach House and The Stable
3.5 star property
Stroud
8.8 out of 10, Excellent, (47 reviews)
"Great stay "
United Kingdom
Tania
$83 nightly
The price is $99
Oct 25 - Oct 26
Total with taxes and fees
The Coach House and The Stable
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

19. Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.6 out of 10, Excellent, (7 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
$93 nightly
The price is $112
Sep 27 - Sep 28
Total with taxes and fees
Lovely 1-bed Loft in Newport
A modern kitchen with white cabinets, a stainless steel range hood, a microwave, and a built-in oven.

20. The Old Bank - yourapartment

The Old Bank - yourapartment
4.0 star property
Brislington
8.0 out of 10, Very good, (5 reviews)
"It's not a bad place. But filthy carpets were the main disappointment & filthy smoke butts outside the main door up stairs. Was there for 3 days, not once did I see anybody do any cleaning or replenish towels or tea & coffee. That's why it wasn't value for money. The owner should put more effort into the place, instead of just taking the money."
Australia
Andre
$258 nightly
The price is $303
Oct 2 - Oct 3
Total with taxes and fees
The Old Bank - yourapartment
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
"Good location, lovely helpful staff. Plenty of lounge space and bar area. Yummy cocktails. Our room and bathroom were spacious and had an iron and hairdryer. Didn't like the digital check in as it had a glitch which meant we couldn't get our room number and had to wait a long time at reception as staff were very busy. Our room was clean but the windows of our room were filthy so hard to see out well. Some of soft furnishings tired and worn ."
Jessica 2-night trip
Posted 1 hour ago
Clayton Hotel Bristol City

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 $70 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: This vacation home rental near 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 you can cook with friends or family.

How many vacation rentals are there in Chepstow?

Choose from 13 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.