Holiday Rentals in Chepstow

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Our top choices for Chepstow holiday rentals

The Snug

The Snug
3.0 star property
Caerwent
The price is €340
includes taxes & fees
25 May - 26 May
The Snug

The Elements Residence

The Elements Residence
Chepstow
The price is €1,065
includes taxes & fees
31 May - 1 Jun
The Elements Residence

Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is €474
includes taxes & fees
18 May - 19 May
Top Lodge

The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is €547
includes taxes & fees
29 May - 30 May
The Honey Pot

Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is €474
includes taxes & fees
20 May - 21 May
Bottom Lodge

Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (24 reviews)
"Amazing place for work or holiday. Clean affordable and great staff"
United Kingdom
Luke
The price is €69
includes taxes & fees
15 May - 16 May
Broadstone Park Camping & Fishery

PYTCHAir Boeing 727 Private Jet Hotel

PYTCHAir Boeing 727 Private Jet Hotel
bristol
The price is €734
includes taxes & fees
14 May - 15 May
PYTCHAir Boeing 727 Private Jet Hotel

Grandads Shack Trevethin Wales

Grandads Shack Trevethin Wales
Pontypool
The price is €458
includes taxes & fees
13 May - 14 May
Grandads Shack Trevethin Wales

Cozy Studio Attic Retreat in Bettws Newydd

Cozy Studio Attic Retreat in Bettws Newydd
3.0 star property
Usk
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Nice grounds. Brand new. Quality finished by master craftsmen. Peaceful"
United Kingdom
Andrew
The price is €98
includes taxes & fees
12 May - 13 May
Cozy Studio Attic Retreat in Bettws Newydd

Newport Student Village - Campus Accommodation

Newport Student Village - Campus Accommodation
4.0 star property
Pillgwenlly
8.2 out of 10, Very good, (221 reviews)
"It's a student halls of residence. If that's what you're expecting I would imagine you'd be very happy with the room. If you're expecting a hotel, it's not a hotel. It was exactly as I was expecting. Comfortable, no frills, perfectly fine for a one night stay for me. Wifi was great. A little bit of noise at times, it's student accommodation, but not too noisy by a long way. I recently stayed at the IBIS in Bristol and that was far noisier. Would happily book again for a short stay."
United Kingdom
Christopher
The price is €76
includes taxes & fees
12 May - 13 May
Newport Student Village - Campus Accommodation

The Sixty 19 Stylish Studios and Apt.

The Sixty 19 Stylish Studios and Apt.
3.0 star property
Adamsdown
The price is €135
includes taxes & fees
12 May - 13 May
The Sixty 19 Stylish Studios and Apt.

The Sixty | Luxury 2BR Apt with Secure Parking

The Sixty | Luxury 2BR Apt with Secure Parking
Adamsdown
The price is €173
includes taxes & fees
12 May - 13 May
The Sixty | Luxury 2BR Apt with Secure Parking

The Old Dairy at Combe Lodge - Hopewell

The Old Dairy at Combe Lodge - Hopewell
North Somerset
8.8 out of 10, Excellent, (10 reviews)
"Great place, Lots of kitchen equipment. Comfy and warm on a cold wintry stay."
United Kingdom
Barbara B.
The price is €179
includes taxes & fees
25 May - 26 May
The Old Dairy at Combe Lodge - Hopewell

Riverfront Flat

Riverfront Flat
3.0 star property
Newport
The price is €226
includes taxes & fees
26 May - 27 May
Riverfront Flat

Blackberry Cottage - Cosy Autumn Getaway in Cardiff

Blackberry Cottage - Cosy Autumn Getaway in Cardiff
Rumney
9.8 out of 10, Exceptional, (6 reviews)
"Great , spacious cottage.. nice rooms and decor Really nice kitchen for sitting and dining :) Highly recommending! "
United Kingdom
Emilia
The price is €162
includes taxes & fees
13 May - 14 May
Blackberry Cottage - Cosy Autumn Getaway in Cardiff

Anstey Heights - Apartment 4 - Hopewell

Anstey Heights - Apartment 4 - Hopewell
Easton
7.4 out of 10, Good, (3 reviews)
"The apartment was easy to find using Google , fairly new and quite welcoming! Lots of useful emails from Hopewell the management company. The layout of the property and its facilities were excellent! However, the whole place needs a very big deep clean! The lounge has a yellow rug on the floor that has definitely seen better days, it was stained and generally nasty. The kitchen utensils all need a good wash before we could use them. The mugs were all stained and also needed a good wash and...
United Kingdom
Nicholas M.
The price is €136
includes taxes & fees
21 May - 22 May
Anstey Heights - Apartment 4 - Hopewell

Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is €235
includes taxes & fees
12 May - 13 May
Orchard by UTDM

Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath

Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath
Dyrham
10.0 out of 10, Exceptional, (15 reviews)
"Just amazing will be staying again"
United Kingdom
Steven L.
The price is €216
includes taxes & fees
28 May - 29 May
Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath

Beautiful 1-bed Cottage in Trellech

Beautiful 1-bed Cottage in Trellech
3.0 star property
Trellech United
9.2 out of 10, Wonderful, (24 reviews)
"Lovely staff and great space to relax."
United Kingdom
Eva
The price is €111
includes taxes & fees
12 May - 13 May
Beautiful 1-bed Cottage in Trellech

The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (132 reviews)
"Awesome hosts and great accommodations!"
United States
Susan
The price is €88
includes taxes & fees
12 May - 13 May
The Priory Cellars Abbots Leigh
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

Everything you need to know about Chepstow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chepstow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chepstow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chepstow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chepstow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chepstow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chepstow holiday rentals we have selected for you start as low as €69 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chepstow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chepstow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chepstow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chepstow?

Yes, there are holiday rentals in Chepstow close to Chepstow Leisure Centre, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chepstow has to offer?

No 2 Georgian Shared House \- By Clifton Short Lets: This holiday home rental outside of Chepstow offers a garden and free WiFi to help you feel comfortable in your new surroundings. Our travellers also rate Large Countryside House sleeps 17 stunning views ,hot tub and Games Rm as a favourite home for rent in Chepstow.

How many holiday rentals are there in Chepstow?

Choose from 9 Expedia holiday rentals in Chepstow for a memorable holiday.

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 holiday rental in Chepstow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chepstow. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for small groups.