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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chepstow vacation rentals

Cottage | Interior

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
$531 nightly
The price is $637
Aug 4 - Aug 5
Total with taxes and fees
The Honey Pot
Fridge, microwave, oven, stovetop

2. The Elements Residence

The Elements Residence
Chepstow
$1,221 nightly
The price is $1,221
Aug 16 - Aug 17
Total with taxes and fees
The Elements Residence
Outdoor dining

3. Top Lodge

Top Lodge
2.0 star property
Caerwent
$457 nightly
The price is $548
Aug 17 - Aug 18
Total with taxes and fees
Top Lodge
Fridge, electric kettle, toaster, cookware/dishes/utensils

4. The Snug

The Snug
3.0 star property
Caerwent
$327 nightly
The price is $393
Aug 3 - Aug 4
Total with taxes and fees
The Snug
Cottage | Living area | Fireplace

5. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
$457 nightly
The price is $548
Aug 17 - Aug 18
Total with taxes and fees
Bottom Lodge
Dining

6. A large group retreat that sleeps 16 guests in 4 bedrooms

A large group retreat that sleeps 16 guests in 4 bedrooms
Chew Stoke
9.8 out of 10, Exceptional, (21 reviews)
"Stunning views in an excellent location, spacious accommodation with a huge garden, we absolutely loved it"
United States
sam h.
$3,106 nightly
The price is $3,106
Aug 2 - Aug 3
Total with taxes and fees
A large group retreat that sleeps 16 guests in 4 bedrooms
Exterior

7. Langford Apartments and Rooms

Langford Apartments and Rooms
3.5 star property
Bristol
8.0 out of 10, Very Good, (1 review)
"I work nights so don’t really get to see anyone but all amenities are here,fair amount of road noise but that’s down to me working nights not the fault of property "
United Kingdom
Michael
$119 nightly
The price is $143
Aug 5 - Aug 6
Total with taxes and fees
Langford Apartments and Rooms
Property entrance

8. Hillcroft Self Catering

Hillcroft Self Catering
3.5 star property
Bristol
9.8 out of 10, Exceptional, (54 reviews)
"Easy parking and super location for flying from Bristol. "
United Kingdom
Tanya
$212 nightly
The price is $254
Aug 9 - Aug 10
Total with taxes and fees
Hillcroft Self Catering
Terrace/patio

9. 6 Newbridge Gardens

6 Newbridge Gardens
3.0 star property
Newbridge
$1,107 nightly
The price is $1,328
Aug 4 - Aug 5
Total with taxes and fees
6 Newbridge Gardens
Front of property

10. Cottage Poppy

Cottage Poppy
2.0 star property
Keynsham
$199 nightly
The price is $239
Aug 3 - Aug 4
Total with taxes and fees
Cottage Poppy
Dining

11. PYTCHAir Boeing 727 Private Jet Hotel

PYTCHAir Boeing 727 Private Jet Hotel
bristol
$847 nightly
The price is $847
Aug 4 - Aug 5
Total with taxes and fees
PYTCHAir Boeing 727 Private Jet Hotel
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, oven, stovetop

12. 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
$179 nightly
The price is $208
Aug 14 - Aug 15
Total with taxes and fees
The Old Bank - yourapartment
2 bedrooms, WiFi, bed sheets

13. Two bedroom apartment in North street with parking

Two bedroom apartment in North street with parking
Southville
10.0 out of 10, Exceptional, (2 reviews)
"Great location on North St. Easy walks to Aston Gate and Bristol City center."
United States
Carl T.
$222 nightly
The price is $222
Aug 23 - Aug 24
Total with taxes and fees
Two bedroom apartment in North street with parking
Lounge

14. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
$220 nightly
The price is $264
Aug 17 - Aug 18
Total with taxes and fees
Orchard by UTDM
Gym

15. The Metalworks

The Metalworks
2.0 star property
Windmill Hill
8.0 out of 10, Very Good, (17 reviews)
"Staff very helpful but check In was a faff and the room was incredibly hot"
United Kingdom
Amy
$103 nightly
The price is $110
Aug 9 - Aug 10
Total with taxes and fees
The Metalworks
Grand Apartment | Living area | 38-inch Smart TV with cable channels

16. Waterside Living I Luxe Apartments

Waterside Living I Luxe Apartments
4.0 star property
Bristol Floating Harbour
9.0 out of 10, Wonderful, (2 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
$236 nightly
The price is $283
Aug 1 - Aug 2
Total with taxes and fees
Waterside Living I Luxe Apartments
Classic House, Private Bathroom | Lounge

17. Ideal Bristol Getaway - 3 bed Harbourside Home

Ideal Bristol Getaway - 3 bed Harbourside Home
2.0 star property
Bristol Floating Harbour
10.0 out of 10, Exceptional, (1 review)
"Good location, recently refurbished, perfect."
United Kingdom
ian
Ideal Bristol Getaway - 3 bed Harbourside Home
TV

18. PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (184 reviews)
"Excellent location, very easy to access all attractions . Spacious apartment "
United Kingdom
Gareth
$100 nightly
The price is $120
Aug 2 - Aug 3
Total with taxes and fees
PREMIER SUITES Bristol Redcliffe
Exterior

19. The Coach House

The Coach House
3.0 star property
Bristol
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful cottage in a great location. Owner is do friendly and helpful"
United Kingdom
Tanya
$347 nightly
The price is $416
Aug 28 - Aug 29
Total with taxes and fees
The Coach House
Classic Studio | Private kitchen | Espresso maker, coffee/tea maker, microwave, electric kettle

20. Hotwells Your Apartment

Hotwells Your Apartment
3.0 star property
Clifton
7.6 out of 10, Good, (9 reviews)
"All excelent"
United States
Juan Sebastian
$527 nightly
The price is $633
Aug 5 - Aug 6
Total with taxes and fees
Hotwells 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

The Bristol Hotel

The Bristol Hotel

10/10 Excellent
"All of the staff were very helpful but especially the barman and restaurant staff. I had an excellent meal in the restaurant, and a great night's sleep. The room was comfortable but I spent precious little time in it to want much more out of the room itself. My single, solitary criticism is a very picky one. There was a hand rail to get into the bath/shower but not one to assist the reverse process. This required a careful balancing act but I descended safely. Thus, a safety rail placed parallel with the rail, which contains the towels might be of benefit to assist those, who like me suffer from arthritis, to exit after bathing or showering. I did not go to the cocktail bar before or after dinner because I was bushed but I will return to Bristol and make sure that I sample its wares."
Mark 1-night trip
Posted 2 hours ago
The Bristol Hotel

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 $77 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 11 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.