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

Chepstow Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chepstow vacation rentals

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is P34,816
P41,779 total
includes taxes & fees
Nov 23 - Nov 24
The Honey Pot

2. The Snug

The Snug
3.0 star property
Caerwent
The price is P22,634
P27,161 total
includes taxes & fees
Nov 19 - Nov 20
The Snug

3. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is P31,594
P37,912 total
includes taxes & fees
Nov 21 - Nov 22
Bottom Lodge

4. Top Lodge

Top Lodge
3.0 star property
Caerwent
The price is P31,594
P37,912 total
includes taxes & fees
Nov 18 - Nov 19
Top Lodge

5. 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 P7,622
P7,622 total
includes taxes & fees
Nov 22 - Nov 23
Beautiful 1-bed Cottage in Trellech

6. Livin' Serviced Apartments - Newport

Livin' Serviced Apartments - Newport
2.0 star property
St Julians
9.6 out of 10, Exceptional, (4 reviews)
"Great apartment. Very spacious. Absolutely loved staying here. Will definitely do it again"
United Kingdom
Lucy
The price is P4,105
P4,926 total
includes taxes & fees
Nov 17 - Nov 18
Livin' Serviced Apartments - Newport

7. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
Bilsham Meadows

8. 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 P6,400
P6,400 total
includes taxes & fees
Nov 15 - Nov 16
The Priory Cellars Abbots Leigh

9. Your Stay Bristol Orchard Gate

Your Stay Bristol Orchard Gate
3.5 star property
Bristol
8.8 out of 10, Excellent, (45 reviews)
"This apartment was clean, warm and had everything we needed. "
United Kingdom
claire
The price is P12,005
P14,406 total
includes taxes & fees
Nov 15 - Nov 16
Your Stay Bristol Orchard Gate

10. Bright & Beautiful Studio Flat in Bristol

Bright & Beautiful Studio Flat in Bristol
3.0 star property
Bristol
10.0 out of 10, Exceptional, (2 reviews)
"Was a beautiful walks away from Bristol City Centre, but transportation is very easily accessible to get to most places. Very quiet, beautiful and was perfect for my holiday! "
United States
Katarina
Bright & Beautiful Studio Flat in Bristol

11. 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 P6,736
P6,736 total
includes taxes & fees
Nov 16 - Nov 17
The Orangery Apartment

12. The Pound

The Pound
3.0 star property
Trellech United
10.0 out of 10, Exceptional, (4 reviews)
"We really loved it there the host was very friendly enjoed the weekend very much"
United Kingdom
Kevin
The price is P24,992
P29,990 total
includes taxes & fees
Dec 13 - Dec 14
The Pound
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chepstow Hotel Reviews

Find out more about Chepstow

Search for holiday rentals in Chepstow on Expedia! You can easily find your home rentals, villas, holiday apartments in Chepstow using one of the methods below:

  • View our selection of featured holiday rentals in Chepstow
  • Use the map to find apartments and other holiday homes in the Chepstow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chepstow while they last

Look no further and take a look at our great range of rental properties in Chepstow!

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.