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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chepstow vacation rentals

Cottage | Interior

The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is ￥85,467
￥102,560 total
includes taxes & fees
Jul 25 - Jul 26
The Honey Pot
Fridge, electric kettle, toaster, cookware/dishes/utensils

The Snug

The Snug
3.0 star property
Caerwent
The price is ￥53,048
￥63,658 total
includes taxes & fees
Jul 22 - Jul 23
The Snug
Cottage | Living area | Fireplace

Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is ￥74,046
￥88,855 total
includes taxes & fees
Jul 25 - Jul 26
Bottom Lodge
Outdoor dining

Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is ￥74,046
￥88,855 total
includes taxes & fees
Aug 2 - Aug 3
Top Lodge
Property grounds

Woodland Cottage Sleeps 5-pet Friendly, Long Stays

Woodland Cottage Sleeps 5-pet Friendly, Long Stays
3.0 star property
Lydbrook
The price is ￥28,577
￥34,292 total
includes taxes & fees
Jul 13 - Jul 14
Woodland Cottage Sleeps 5-pet Friendly, Long Stays
Fridge, electric kettle, toaster, cookware/dishes/utensils

Rabbit Hill Hut

Rabbit Hill Hut
2.0 star property
Abergavenny
The price is ￥54,890
￥65,868 total
includes taxes & fees
Jul 25 - Jul 26
Rabbit Hill Hut
Miscellaneous

Tysylfaen Brecon Beacons

Tysylfaen Brecon Beacons
3.0 star property
Crickhowell
The price is ￥35,930
￥35,930 total
includes taxes & fees
Jul 12 - Jul 13
Tysylfaen Brecon Beacons
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, oven, stovetop

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
The price is ￥34,618
￥46,986 total
includes taxes & fees
Jul 17 - Jul 18
The Old Bank - yourapartment
Family Apartment | Living area | 42-inch Smart TV with satellite channels, Netflix, streaming services

The Sixty 19 Stylish Studios and Apt.

The Sixty 19 Stylish Studios and Apt.
3.0 star property
Adamsdown
The price is ￥11,058
￥26,272 total
includes taxes & fees
Jul 13 - Jul 14
The Sixty 19 Stylish Studios and Apt.
Property grounds

The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (135 reviews)
"Excellent place to stay,I would highly recommend!"
United Kingdom
Ray
The price is ￥16,469
￥16,469 total
includes taxes & fees
Jul 23 - Jul 24
The Priory Cellars Abbots Leigh
Gym

The Metalworks

The Metalworks
2.0 star property
Windmill Hill
9.0 out of 10, Wonderful, (8 reviews)
"Great accommodation Clean Great complementary beer Will be staying there again aoon"
United Kingdom
Pankaj
The price is ￥5,506
￥17,443 total
includes taxes & fees
Jul 18 - Jul 19
The Metalworks
Classic Apartment, Private Bathroom | Garden

Charming Flat With Private Patio in Clifton

Charming Flat With Private Patio in Clifton
3.5 star property
Clifton
10.0 out of 10, Exceptional, (1 review)
"Clean, spacious, good location, lovely place to stay"
United Kingdom
James
Charming Flat With Private Patio in Clifton
Exterior

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
The price is ￥20,573
￥24,688 total
includes taxes & fees
Jul 12 - Jul 13
Langford Apartments and Rooms
TV

PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (183 reviews)
"Excellent location, very easy to access all attractions . Spacious apartment "
United Kingdom
Gareth
The price is ￥16,073
￥19,287 total
includes taxes & fees
Jul 19 - Jul 20
PREMIER SUITES Bristol Redcliffe
Exterior

6 Bed House Sleeps 13 - Private Garden

6 Bed House Sleeps 13 - Private Garden
4.0 star property
Bristol
The price is ￥38,560
￥46,272 total
includes taxes & fees
Jul 16 - Jul 17
6 Bed House Sleeps 13 - Private Garden
Exterior

Rose Cottage

Rose Cottage
3.0 star property
Hereford
The price is ￥69,257
￥83,108 total
includes taxes & fees
Jul 15 - Jul 16
Rose Cottage
Apartment, 1 Bedroom (Rosie) | Travel crib, bed sheets, wheelchair access

The Old Stables

The Old Stables
3.5 star property
Ynysddu
9.6 out of 10, Exceptional, (8 reviews)
"Immaculate, quiet, warm and incredibly spacious. A very nice place to stay. "
United Kingdom
Matt
The price is ￥22,934
￥27,521 total
includes taxes & fees
Jul 13 - Jul 14
The Old Stables
Terrace/patio

The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (77 reviews)
"Wonderful property and hosts. Great parking and facilities in property with plenty of space and stocked kitchen facilities. Would stay again"
United Kingdom
Janet
The price is ￥14,735
￥14,735 total
includes taxes & fees
Jul 23 - Jul 24
The Orangery Apartment
Basic Apartment | Private kitchen | Full-size fridge, microwave, oven, stovetop

YourApartment - Wellington Place

YourApartment - Wellington Place
3.0 star property
Hambrook
6.0 out of 10, (2 reviews)
"Thanks for the stay traveled with a baby for 2 days check out is 10 am how ever there was no fuss checking out at 10:30 fault of my own cleaning up the pots and pans I used"
United Kingdom
Jadeleigh
The price is ￥32,931
￥39,518 total
includes taxes & fees
Jul 17 - Jul 18
YourApartment - Wellington Place
Grand Apartment | Living area | 38-inch Smart TV with cable channels

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
The price is ￥51,094
￥61,312 total
includes taxes & fees
Jul 31 - Aug 1
Waterside Living I Luxe Apartments
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
"Great location right on harbor with nice walk along river bay with many coffee & pastry shops."
Dennis 2-night trip
Posted 11 hours ago
The Bristol Hotel

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?

Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub : This vacation home near Chepstow offers a fireplace, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.