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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chepstow vacation rentals

Cottage | Interior

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is ￥85,554
￥102,665 total
includes taxes & fees
Aug 29 - Aug 30
The Honey Pot
Living area

2. The Elements Residence

The Elements Residence
Chepstow
The price is ￥173,537
￥198,266 total
includes taxes & fees
Aug 30 - Aug 31
The Elements Residence
Cottage | Living area

3. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is ￥74,122
￥88,946 total
includes taxes & fees
Aug 31 - Sep 1
Bottom Lodge
Cottage

4. Ferryman's Lodge

Ferryman's Lodge
2.0 star property
Chepstow
The price is ￥61,823
￥74,188 total
includes taxes & fees
Sep 24 - Sep 25
Ferryman's Lodge
Private kitchen

5. The Snug

The Snug
3.0 star property
Caerwent
The price is ￥53,102
￥63,722 total
includes taxes & fees
Aug 31 - Sep 1
The Snug
Outdoor dining

6. Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is ￥74,122
￥88,946 total
includes taxes & fees
Sep 14 - Sep 15
Top Lodge
Property grounds

7. The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (137 reviews)
"Lovely host, great location and a unique spacious accommodation with a few thoughtful extras."
United Kingdom
Le-Anne
The price is ￥16,486
￥16,486 total
includes taxes & fees
Aug 31 - Sep 1
The Priory Cellars Abbots Leigh
Property grounds

8. HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation
Lydney
10.0 out of 10, Exceptional, (30 reviews)
"A great property with a few clearly defined spaces to enjoy. The location was great for an enjoyable pleasant weekend, and the process with the host was very efficient and slick."
United Kingdom
Samuel P.
The price is ￥162,691
￥185,251 total
includes taxes & fees
Aug 27 - Aug 28
HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation
Cottage | Interior

9. 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 ￥58,449
￥70,139 total
includes taxes & fees
Sep 11 - Sep 12
The Pound
Cottage | Property entrance

10. 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 ￥20,260
￥20,260 total
includes taxes & fees
Sep 8 - Sep 9
Beautiful 1-bed Cottage in Trellech
Interior

11. A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
Alvington
10.0 out of 10, Exceptional, (18 reviews)
"Very enjoyable stay would try to re-book when next in the area"
United States
Philip R.
The price is ￥21,475
￥30,586 total
includes taxes & fees
Aug 31 - Sep 1
A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
Living area

12. 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 ￥31,725
￥38,070 total
includes taxes & fees
Aug 31 - Sep 1
Your Stay Bristol Orchard Gate
Living area

13. Cider Press Barn - UK12379

Cider Press Barn - UK12379
Lydney
10.0 out of 10, Exceptional, (8 reviews)
"Ideally situated for trips into the Forest.Wonderful accommodation, well equipped and excellent hosts on hand."
United States
John Littlewood
The price is ￥76,573
￥76,573 total
includes taxes & fees
Sep 12 - Sep 13
Cider Press Barn - UK12379
Suite, 1 Bedroom

14. Redmayne House

Redmayne House
3.5 star property
Clifton
9.4 out of 10, Exceptional, (40 reviews)
"Lovely place to stay"
United Kingdom
Gail
The price is ￥24,189
￥29,027 total
includes taxes & fees
Aug 27 - Aug 28
Redmayne House
Terrace/patio

15. The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (78 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 ￥17,354
￥17,354 total
includes taxes & fees
Aug 31 - Sep 1
The Orangery Apartment
Panoramic Studio, Private Bathroom | Exterior

16. 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
The price is ￥25,597
￥38,612 total
includes taxes & fees
Aug 31 - Sep 1
Bright & Beautiful Studio Flat in Bristol
Room

17. One Bedroom Apartment Close to MOD

One Bedroom Apartment Close to MOD
Bristol
8.0 out of 10, Very Good, (2 reviews)
"Everything in the property is well maintained ."
United Kingdom
Chijioke I.
The price is ￥15,835
￥25,596 total
includes taxes & fees
Aug 30 - Aug 31
One Bedroom Apartment Close to MOD
Premium Apartment, 2 Bedrooms | Living area

18. Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.4 out of 10, Very Good, (157 reviews)
"Fast and easy check-in, helpful staff and quick production of a VAT invoice for expenses. The apartment was clean, roomy and comfortable, with a good bed, large TV, well equipped kitchen and great shower too. Parking is very convenient and placed at the back of the building in the multi-storey car park. Local supermarket very close too. Great."
United Kingdom
Andrew
The price is ￥11,592
￥13,911 total
includes taxes & fees
Aug 27 - Aug 28
Quay Apartments Clarence House
Cottage | Dining

19. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is ￥262,377
￥314,852 total
includes taxes & fees
Aug 31 - Sep 1
Bilsham Meadows
Studio | Exterior

20. Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.8 out of 10, Excellent, (5 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is ￥15,257
￥18,309 total
includes taxes & fees
Aug 27 - Aug 28
Lovely 1-bed Loft in Newport
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
"Clean rooms. Equipped with essentials. Breakfast provided if you need it , although we never ate there. Excellent location - being in the city center means proximity to great coffee shops and restaurants , all within walking distance. Easy to get an Uber anywhere else. This hotel also has parking if you rent a car."
Parvathavardhini 5-night trip
Posted 6 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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  • 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?

Beautifully converted stone barn with amazing views towards the black mountains : This vacation home rental near Chepstow is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Chepstow?

Choose from 13 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.