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

Chepstow Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 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
$552 nightly
The price is $663
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
$501 nightly
The price is $601
Nov 13 - Nov 14
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
$359 nightly
The price is $431
Nov 19 - Nov 20
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
3.0 star property
Caerwent
$501 nightly
The price is $601
Nov 13 - Nov 14
Total with taxes and fees
Top Lodge
An outdoor patio with a round glass table surrounded by wicker chairs, a barbecue grill, and a hot tub under a wooden pergola.

5. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
$1,773 nightly
The price is $2,128
Nov 30 - Dec 1
Total with taxes and fees
Bilsham Meadows
A historic stone bridge with a moat, surrounded by modern buildings and a railway track.

6. Livin' Serviced Apartments - Newport

Livin' Serviced Apartments - Newport
2.0 star property
St Julians
10.0 out of 10, Exceptional, (3 reviews)
"Great apartment. Very spacious. Absolutely loved staying here. Will definitely do it again"
United Kingdom
Lucy
$49 nightly
The price is $59
Nov 17 - Nov 18
Total with taxes and fees
Livin' Serviced Apartments - Newport
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
Nov 12 - Nov 13
Total with taxes and fees
PREMIER SUITES Bristol Redcliffe
A stone wall entrance to a building with a black door and a small trash bin.

8. 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
$120 nightly
The price is $120
Nov 22 - Nov 23
Total with taxes and fees
Beautiful 1-bed Cottage in Trellech
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

9. 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
$214 nightly
The price is $256
Nov 20 - Nov 21
Total with taxes and fees
Frederick Place Your Apartment
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.

10. Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.6 out of 10, Excellent, (162 reviews)
"Convenient location close to train station, safe area, clean and has all the amenities needed. Will stay again"
United Kingdom
KONSTANTINOS
$77 nightly
The price is $92
Nov 29 - Nov 30
Total with taxes and fees
Quay Apartments Clarence House
A modern hotel room with a large bed, a small sitting area, a kitchenette, and a bathroom.

11. Your Apartment I Clifton Village

Your Apartment I Clifton Village
4.0 star property
Clifton
7.4 out of 10, Good, (113 reviews)
"A great location in central Clifton, had everything we needed and easily accesible"
United Kingdom
Erin
$125 nightly
The price is $151
Nov 20 - Nov 21
Total with taxes and fees
Your Apartment I Clifton Village
A historic building with a stone facade, large windows, and a gated entrance.

12. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (85 reviews)
"The apartment was so roomy . Space to park and a great little pub at the end of the road . Nick was an excellent host !"
Australia
Narelle
$107 nightly
The price is $107
Nov 12 - Nov 13
Total with taxes and fees
The Orangery Apartment
A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

13. 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)
"Great little apartment which is well located for the centre of Bristol and the docks and near plenty of pubs and restaurants. We used it as a base for some historical touristy walks in the area, everything is within walking distance"
United Kingdom
Amanda
$160 nightly
The price is $192
Nov 16 - Nov 17
Total with taxes and fees
Higgihaus 26 Clare Street Aparthotel
A modern kitchen with white cabinets, a built-in oven, and a stainless steel range hood.

14. Your Apartment Clifton House

Your Apartment Clifton House
3.0 star property
Bristol
7.4 out of 10, Good, (118 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
$124 nightly
The price is $148
Nov 12 - Nov 13
Total with taxes and fees
Your Apartment Clifton House
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
2.0 star property
Bristol
$1,615 nightly
The price is $1,938
Nov 16 - Nov 17
Total with taxes and fees
Hidden Well
A historic building with a stone facade, large windows, and a gated entrance.

16. 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
$101 nightly
The price is $101
Nov 15 - Nov 16
Total with taxes and fees
The Priory Cellars Abbots Leigh
A modern building with a brick facade and large windows.

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, (222 reviews)
"Excellent….. Will definitely stay again on my next overnight stay A******"
United Kingdom
Allie
$99 nightly
The price is $119
Nov 15 - Nov 16
Total with taxes and fees
PREMIER SUITES PLUS Bristol Cabot Circus
A modern kitchen with a black countertop, a hanging rack, and a microwave.

18. 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
$117 nightly
The price is $141
Nov 12 - Nov 13
Total with taxes and fees
Hotwells Your Apartment
A multi-story building with a stone facade, large windows, and a corner entrance.

19. Your Apartment - Pembroke House

Your Apartment - Pembroke House
4.0 star property
Clifton
8.8 out of 10, Excellent, (10 reviews)
"Beautiful property in beautiful Clifton. Will definitely book again if i'm ever in Bristol!"
Netherlands
reihana
$139 nightly
The price is $167
Nov 11 - Nov 12
Total with taxes and fees
Your Apartment - Pembroke House
A modern bedroom with a large bed, a bedside table with a lamp, and a view of the city through a window.

20. 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
$154 nightly
The price is $184
Nov 12 - Nov 13
Total with taxes and fees
Colston Street - Your Apartment
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

Celtic Manor Resort

Celtic Manor Resort

10/10 Excellent
"Lovely hotel which is perfect for business or leisure trips. Spacious well appointed rooms, superb service, but the absolute standout for me was the exceptional spa facilities. The hot tub extends the length of the pool, it’s the biggest I’ve ever seen! Lovely way to relax after a long day."
Victoria 1-night trip
Posted less than an hour ago
Celtic Manor Resort

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 $92 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.