130+ Private Villas and Holiday Rentals in Chepstow |
Chepstow Holiday Rentals
Cottage
9.8Exceptional
(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
د.إ.1,230/Night
7 Nights - د.إ.8,612
House
10.0Exceptional
(37 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
د.إ.683/Night
7 Nights - د.إ.4,782
Cottage
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Pet Friendly
Parking
Internet
د.إ.1,143/Night
7 Nights - د.إ.8,003
Cabin
Anne's Hut offers a romantic retreat for two in two interlinked shepherd's huts with decking area an
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.983/Night
7 Nights - د.إ.6,882
Apartment
10.0Exceptional
(8 Reviews)
3 Bedrooms
3 Baths
6 Guests
699.65 ft²
- Parking
- Internet
Child Friendly
Security/Safety
د.إ.598/Night
7 Nights - د.إ.4,187
Cottage
10.0Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
4 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.865/Night
7 Nights - د.إ.6,052
Cottage
8.0Excellent
(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.656/Night
7 Nights - د.إ.4,591
Cottage
10.0Exceptional
(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
1281 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,148/Night
7 Nights - د.إ.8,036
Cottage
10.0Exceptional
(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.1,632/Night
7 Nights - د.إ.11,425
Luxury Holiday Rentals in Chepstow
Over 121+ Luxury Holiday Rentals in or Near Chepstow
House
6 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.4,917/Night
7 Nights - د.إ.34,420
Cottage
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
Pool- Balcony/Terrace
د.إ.4,713/Night
7 Nights - د.إ.32,991
House
10 Bedrooms
8 Baths
26 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.4,427/Night
7 Nights - د.إ.30,986
New
House
4 Bedrooms
3 Baths
9 Guests
322.92 ft²
- Hot Tub
- Fireplace/Heating
- View
- Parking
د.إ.3,332/Night
7 Nights - د.إ.23,325
House
8.6Fabulous
(7 Reviews)
7 Bedrooms
4 Baths
17 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.3,299/Night
7 Nights - د.إ.23,093
House
9.8Exceptional
(6 Reviews)
7 Bedrooms
4 Baths
17 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.3,230/Night
7 Nights - د.إ.22,612
New
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
9 Guests
322.92 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
د.إ.2,704/Night
7 Nights - د.إ.18,932
Apartment
10 Bedrooms
8 Baths
22 Guests
2960.08 ft²
- View
- Parking
- Internet
- Child Friendly
د.إ.2,465/Night
7 Nights - د.إ.17,254
New
House
4 Bedrooms
2 Baths
9 Guests
322.92 ft²
- Balcony/Terrace
- Parking
- Internet
- Child Friendly
د.إ.2,388/Night
7 Nights - د.إ.16,714
Top-Rated Holiday Rentals with a Pool in Chepstow
Over 4+ The Best Private Villas and Holiday Rentals in Chepstow with a Pool
Hotel
8.2Excellent
(1001 Reviews)
1 Bath
- Hot Tub
Spa- Fireplace/Heating
- Pool
د.إ.483/Night
7 Nights - د.إ.3,386
Hotel
8.1Excellent
(2136 Reviews)
8 Baths
326.95 ft²
Private Pool- Hot Tub
- Spa
- Fireplace/Heating
د.إ.547/Night
7 Nights - د.إ.3,827
Villa
1 Bedroom
1 Bath
10 Guests
- Private Pool
- Pool
- Pet Friendly
- Kitchen
د.إ.3,522/Night
7 Nights - د.إ.24,654
Cottage
5 Bedrooms
4 Baths
10 Guests
1722 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
د.إ.3,041/Night
7 Nights - د.إ.21,286
Pet-Friendly Holiday Rentals in Chepstow
Over 52+ Pet-Friendly Holiday Rentals in or Near Chepstow
Cottage
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.702/Night
7 Nights - د.إ.4,910
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1280.91 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
د.إ.1,447/Night
7 Nights - د.إ.10,129
House
4.3Average
(22 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
د.إ.369/Night
7 Nights - د.إ.2,582
Cabin
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
301 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.944/Night
7 Nights - د.إ.6,607
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
10.76 ft²
- View
- Pet Friendly
- Internet
Sports/Activities
د.إ.1,060/Night
7 Nights - د.إ.7,419
Cottage
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.524/Night
7 Nights - د.إ.3,665
Cottage
10.0Exceptional
(3 Reviews)
4 Bedrooms
1 Bath
7 Guests
1808 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,238/Night
7 Nights - د.إ.8,667
Cottage
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.801/Night
7 Nights - د.إ.5,604
Cabin
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
162 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.690/Night
7 Nights - د.إ.4,829
Large Holiday Rentals and Private Villas in Chepstow
Over 15+ Large Holiday Rentals and Private Villas in or Near Chepstow
Cottage
2.0Average
(1 Review)
5 Bedrooms
5 Baths
10 Guests
2314 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,733/Night
7 Nights - د.إ.12,127
House
9.5Exceptional
(48 Reviews)
5 Bedrooms
5 Baths
11 Guests
864.7 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
د.إ.336/Night
7 Nights - د.إ.2,350
House
7 Bedrooms
4 Baths
28 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
د.إ.6,751/Night
7 Nights - د.إ.47,252
House
9.3Exceptional
(689 Reviews)
7 Bedrooms
7 Baths
14 Guests
172.22 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Breakfast
د.إ.569/Night
7 Nights - د.إ.3,985
House
6 Bedrooms
3 Baths
14 Guests
3229 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.3,799/Night
7 Nights - د.إ.26,593
Bed & Breakfast
8.4Excellent
(661 Reviews)
7 Bedrooms
7 Baths
16 Guests
93.8 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
د.إ.267/Night
7 Nights - د.إ.1,866
Cottage
5 Bedrooms
3 Baths
10 Guests
1722 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,226/Night
7 Nights - د.إ.8,583
House
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
10 Guests
2300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.2,367/Night
7 Nights - د.إ.16,567
Villa
7 Bedrooms
4 Baths
28 Guests
- Kitchen
- Internet
- Child Friendly
Laundry
د.إ.7,156/Night
7 Nights - د.إ.50,094
Wheelchair Accessible Holiday Homes in Chepstow
Over 4+ Wheelchair Accessible Holiday Homes in or Near Chepstow
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
د.إ.551/Night
7 Nights - د.إ.3,853
Hotel
9.3Exceptional
(306 Reviews)
9 Baths
272.68 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
د.إ.679/Night
7 Nights - د.إ.4,752
Hotel
8.7Fabulous
(1694 Reviews)
5 Baths
219.59 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
Air Conditioner
د.إ.437/Night
7 Nights - د.إ.3,063
Hotel
7.7Very Good
(1614 Reviews)
4 Baths
177.61 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
د.إ.408/Night
7 Nights - د.إ.2,854
Chepstow Private Villas and Holiday Homes Under $200
Over 44+ Chepstow Private Villas and Holiday Homes Under $200
Cottage
- Cardiff
- ·
- Llanvair Discoed
- 0.66 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.626/Night
7 Nights - د.إ.4,381
House
9.8Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
1076.39 ft²
- View
- Parking
- Internet
Barbecue/Outdoor Cooking
د.إ.599/Night
7 Nights - د.إ.4,198
New
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
د.إ.638/Night
7 Nights - د.إ.4,466
House
9.7Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
161.46 ft²
- Hot Tub
- Fireplace/Heating
- View
- Pet Friendly
د.إ.641/Night
7 Nights - د.إ.4,488
Cottage
1 Bedroom
1 Bath
2 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Child Friendly
د.إ.523/Night
7 Nights - د.إ.3,662
House
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
د.إ.544/Night
7 Nights - د.إ.3,805
Hotel
9.8Exceptional
(18 Reviews)
1 Bath
344 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Internet
د.إ.504/Night
7 Nights - د.إ.3,529
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
646 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.426/Night
7 Nights - د.إ.2,982
Instantly Bookable Holiday Homes in Chepstow
Over 26+ Instantly Bookable Holiday Homes in or Near Chepstow
Cottage
Orchard holiday cottage is a beautiful romantic dwelling ideal for couples. This perfect property is
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.936/Night
7 Nights - د.إ.6,552
Cottage
9.8Exceptional
(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.815/Night
7 Nights - د.إ.5,707
Cottage
9.6Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,197/Night
7 Nights - د.إ.8,381
Cottage
9.4Exceptional
(18 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.746/Night
7 Nights - د.إ.5,222
Cottage
9.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.972/Night
7 Nights - د.إ.6,802
Cottage
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,374/Night
7 Nights - د.إ.9,615
Cottage
3 Bedrooms
3 Baths
6 Guests
1550 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.2,015/Night
7 Nights - د.إ.14,103
Cottage
3 Bedrooms
4 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,862/Night
7 Nights - د.إ.13,030
Cottage
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,630/Night
7 Nights - د.إ.11,411
Book a Last Minute Place to Stay in Chepstow
About Casai's Private Villas and Holiday Rentals in Chepstow
Discover more than 130 vacation rentals available in Chepstow. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chepstow.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chepstow, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chepstow. On average, places to stay near Chepstow offer 396.85 ft², with nightly prices averaging د.إ.1,184.
With Casai, finding and comparing holiday rentals in Chepstow is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Chepstow
| Type | Count |
|---|---|
| Vacation Homes | 54 |
| Cottages | 36 |
| Holiday Apartments | 15 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Chepstow
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chepstow.
Weather in Chepstow, GB
View the weather forecast for Chepstow before booking your Chepstow Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 32°F
March - May
High 61°F Low 36°F
June - August
High 63°F Low 48°F
September - November
High 58°F Low 35°F
Top Attractions Around Chepstow, GB
Casai offers a large selection of top attractions around Chepstow . Research things to do on your vacation before you visit Chepstow.
Other Places to Stay in Chepstow, GB
Frequently Asked Questions About Chepstow?
What are the top holiday rentals in Chepstow?
With numerous options available in Chepstow, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chepstow:
- The Potting Shed at Mathern Palace
- Wallhope Retreat - Chepstow, spectacular views
- Cider Mill Lodge - HW7420
- Welsh Marches - Sugar Loaf
- The Royal George
- Welsh Marches - Blorenge
- New 3 Bedroom Flat Close to Station
- Welsh Gatehouse: Historical Castle with EV Charger
- The Honey Pot
- Welsh Marches at Upper Glyn Farm
Which holiday homes in Chepstow are best for families?
If you're searching for a family-friendly holiday home in Chepstow, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chepstow:
- 2 bedroom accommodation in Chepstow
- Vauxhall Cottage, Chepstow - 4 Bedroom Pet-Friendly Home with Private Fenced Garden, Walk to Town and Castle
- No.8 Accommodation
How many Casai.ae holiday rentals are available in Chepstow?
As of 2026, Casai boasts over 130 properties listed in the Chepstow area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chepstow.
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Finding the best prices in Chepstow
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