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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chepstow vacation rentals

A covered outdoor seating area with a pergola, wooden benches, and a table with a bottle and glasses.

1. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is P23,589
P28,307 total
includes taxes & fees
Oct 8 - Oct 9
Ferryman's Lodge
A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

2. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is P32,644
P39,173 total
includes taxes & fees
Oct 17 - Oct 18
The Honey Pot
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
The price is P20,262
P24,314 total
includes taxes & fees
Oct 13 - Oct 14
The Snug
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

4. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is P28,325
P33,990 total
includes taxes & fees
Oct 18 - Oct 19
Top Lodge
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
The price is P28,282
P33,939 total
includes taxes & fees
Oct 11 - Oct 12
Bottom Lodge
A stone wall entrance to a building with a black door and a small trash bin.

6. 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 P7,492
P7,492 total
includes taxes & fees
Oct 4 - Oct 5
Beautiful 1-bed Cottage in Trellech
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
The price is P4,138
P4,966 total
includes taxes & fees
Oct 4 - Oct 5
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
The price is P6,290
P6,290 total
includes taxes & fees
Oct 5 - Oct 6
The Priory Cellars Abbots Leigh
A spacious lobby with a large sofa, patterned chairs, a wooden coffee table, and a large window offering a view of the street.

9. Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is P5,339
P16,339 total
includes taxes & fees
Oct 28 - Oct 29
Orchard by UTDM
A conservatory with stone arches, potted plants, and a bench.

10. 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
The price is P6,622
P6,622 total
includes taxes & fees
Oct 4 - Oct 5
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.

11. 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
The price is P7,087
P12,080 total
includes taxes & fees
Oct 4 - Oct 5
Higgihaus 26 Clare Street Aparthotel
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.

12. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is P100,114
P120,137 total
includes taxes & fees
Oct 12 - Oct 13
Bilsham Meadows
A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

13. 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
The price is P5,877
P7,052 total
includes taxes & fees
Oct 4 - Oct 5
Lovely 1-bed Loft in Newport
A modern kitchen with wooden cabinets, a dining table with chairs, and large windows with curtains.

14. 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, (217 reviews)
"Great location next to the shops and 1 min to some restaurants, or ten mins walk to the bars and restaurants by the river. Apartment was amazing. Two bedrooms, two bathrooms. Kitchen with microwave. Clean and very spacious."
United Kingdom
GILLIAN
The price is P6,139
P7,366 total
includes taxes & fees
Oct 4 - Oct 5
PREMIER SUITES PLUS Bristol Cabot Circus
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

Mollie's Bristol

Mollie's Bristol

10/10 Excellent
"Really excellent place to stop overnight to break up a long journey."
Jo 1-night trip
Posted 2 hours ago
Mollie's Bristol

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
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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.