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

Chepstow Vacation Rentals

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Our top choices for Chepstow vacation rentals

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is CA $779
CA $934 total
includes taxes & fees
Nov 24 - Nov 25
The Honey Pot

2. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is CA $707
CA $848 total
includes taxes & fees
Nov 13 - Nov 14
Bottom Lodge

3. The Snug

The Snug
3.0 star property
Caerwent
The price is CA $506
CA $607 total
includes taxes & fees
Nov 19 - Nov 20
The Snug

4. Top Lodge

Top Lodge
3.0 star property
Caerwent
The price is CA $707
CA $848 total
includes taxes & fees
Nov 12 - Nov 13
Top Lodge

5. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is CA $2,501
CA $3,001 total
includes taxes & fees
Dec 2 - Dec 3
Bilsham Meadows

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
The price is CA $77
CA $92 total
includes taxes & fees
Nov 8 - Nov 9
Livin' Serviced Apartments - Newport

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 CA $140
CA $168 total
includes taxes & fees
Nov 8 - Nov 9
PREMIER SUITES Bristol Redcliffe

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
The price is CA $165
CA $165 total
includes taxes & fees
Nov 29 - Nov 30
Beautiful 1-bed Cottage in Trellech

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
The price is CA $292
CA $351 total
includes taxes & fees
Nov 20 - Nov 21
Frederick Place Your Apartment

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
The price is CA $109
CA $130 total
includes taxes & fees
Dec 6 - Dec 7
Quay Apartments Clarence House

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
The price is CA $188
CA $226 total
includes taxes & fees
Nov 10 - Nov 11
Your Apartment I Clifton Village

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
The price is CA $151
CA $151 total
includes taxes & fees
Nov 11 - Nov 12
The Orangery Apartment

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
The price is CA $145
CA $256 total
includes taxes & fees
Nov 8 - Nov 9
Higgihaus 26 Clare Street Aparthotel

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
The price is CA $178
CA $214 total
includes taxes & fees
Nov 12 - Nov 13
Your Apartment Clifton House

15. Hidden Well

Hidden Well
2.0 star property
Bristol
The price is CA $2,278
CA $2,733 total
includes taxes & fees
Nov 11 - Nov 12
Hidden Well

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
The price is CA $143
CA $143 total
includes taxes & fees
Nov 17 - Nov 18
The Priory Cellars Abbots Leigh

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)
"Excellent….. Will definitely stay again on my next overnight stay A******"
United Kingdom
Allie
The price is CA $140
CA $168 total
includes taxes & fees
Nov 8 - Nov 9
PREMIER SUITES PLUS Bristol Cabot Circus

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
The price is CA $166
CA $199 total
includes taxes & fees
Nov 8 - Nov 9
Hotwells Your Apartment

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
The price is CA $180
CA $215 total
includes taxes & fees
Nov 8 - Nov 9
Your Apartment - Pembroke House

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
The price is CA $190
CA $228 total
includes taxes & fees
Nov 13 - Nov 14
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

Find out more about Chepstow

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chepstow. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.