Welsh Gatehouse A Historic Castle Retreat that Welcomes Dogs and Electric Vehicles 
Best Price Match
9.3 (45 Reviews) Holiday_home
The entire place is yours • 32 m² size • Free on-site parking
Best Price Match 36+ Vacation Rentals Near Chepstow
NearbyHoliday - Vacation Rentals in Chepstow
Gardener's Cottage at Mathern Palace Best Price Match
9.5 (59 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match 
The Potting Shed at Mathern Palace Best Price Match
10.0 (36 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match 
Chateau Terrace Georgian House Best Price Match
8.7 (88 Reviews) Homestay
Pet friendly • Free WiFi • View
Best Price Match 
Broadrock Accommodation - Clock Cottage Best Price Match
9.5 (44 Reviews) Apartment
The entire place is yours • 278 m² size • Free on-site parking
Best Price Match 
20 Fairview Chepstow Best Price Match
9.1 (67 Reviews) Holiday_home
The entire place is yours • 20 m² size • Free on-site parking
Best Price Match 
Number 10 Best Price Match
8.7 (63 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Free WiFi
Best Price Match 
Sedbury Farm Cottages Best Price Match
8.4 (156 Reviews) Apartment
Apartments • Free on-site parking • Free WiFi
Best Price Match Luxury Places to Stay in Chepstow
Over 32+ Luxury Places to Stay in or Near Chepstow
Delta Hotels by Marriott St Pierre Country Club Best Price Match
8.2 (2131 Reviews) Hotel
Breakfast • Free on-site parking • Indoor swimming pool
Best Price Match 
Two Rivers Lodge by Marston’s Inns Best Price Match
8.7 (1702 Reviews) Hotel
Breakfast • Free on-site parking • Restaurant
Best Price Match Welsh Gatehouse A Historic Castle Retreat that Welcomes Dogs and Electric Vehicles Best Price Match
9.3 (45 Reviews) Holiday_home
The entire place is yours • 32 m² size • Free on-site parking
Best Price Match Broadrock Accommodation - Clock Cottage Best Price Match
9.5 (44 Reviews) Apartment
The entire place is yours • 278 m² size • Free on-site parking
Best Price Match 
Vauxhall Cottage, Chepstow - 4 Bedroom Pet-Friendly Home with Private Fenced Garden, Walk to Town and Castle Best Price Match
9.9 (9 Reviews) Holiday_home
The entire place is yours • 168 m² size • Free on-site parking
Best Price Match 
Welsh Apple Barn Best Price Match
9.7 (15 Reviews) Holiday_home
The entire place is yours • 100 m² size • Free on-site parking
Best Price Match 
The Royal George Best Price Match
9.3 (301 Reviews) Hotel
Breakfast • Free on-site parking • Restaurant
Best Price Match Pet-Friendly Vacation Rentals in Chepstow
Over 21+ Pet-Friendly Vacation Rentals in or Near Chepstow
Delta Hotels by Marriott St Pierre Country Club Pets allowed Best Price Match
8.2 (2131 Reviews) Hotel
Breakfast • Free on-site parking • Indoor swimming pool
Best Price Match 
The Beaufort Hotel Pets allowed Best Price Match
7.7 (1614 Reviews) Hotel
Breakfast • Free on-site parking • Pet friendly
Best Price Match 
Castle View Hotel Pets allowed Best Price Match
7.2 (564 Reviews) Bed_and_breakfast
Breakfast • Pet friendly • Free WiFi
Best Price Match Vauxhall Cottage, Chepstow - 4 Bedroom Pet-Friendly Home with Private Fenced Garden, Walk to Town and Castle Pets allowed Best Price Match
9.9 (9 Reviews) Holiday_home
The entire place is yours • 168 m² size • Free on-site parking
Best Price Match 
Wallhope Retreat Pets allowed Best Price Match
10.0 (3 Reviews) Holiday_home
The entire place is yours • 119 m² size • Free on-site parking
Best Price Match 
The Old Dairy Pets allowed Best Price Match
9.8 (6 Reviews) Holiday_home
The entire place is yours • 13 m² size • Free on-site parking
Best Price Match 
Court Park Barn Pets allowed Best Price Match
9.0 (3 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Hot tub
Best Price Match 
Edge Barn Pets allowed Best Price Match
9.6 (183 Reviews) Holiday_home
The entire place is yours • 110 m² size • Free on-site parking
Best Price Match Vacation Rentals in Chepstow
Over 36+ Vacation Rentals in or Near Chepstow
Welsh Gatehouse A Historic Castle Retreat that Welcomes Dogs and Electric Vehicles Best Price Match
9.3 (45 Reviews) Holiday_home
The entire place is yours • 32 m² size • Free on-site parking
Best Price Match Gardener's Cottage at Mathern Palace Best Price Match
9.5 (59 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match The Potting Shed at Mathern Palace Best Price Match
10.0 (36 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match Chateau Terrace Georgian House Best Price Match
8.7 (88 Reviews) Homestay
Pet friendly • Free WiFi • View
Best Price Match Broadrock Accommodation - Clock Cottage Best Price Match
9.5 (44 Reviews) Apartment
The entire place is yours • 278 m² size • Free on-site parking
Best Price Match 20 Fairview Chepstow Best Price Match
9.1 (67 Reviews) Holiday_home
The entire place is yours • 20 m² size • Free on-site parking
Best Price Match Number 10 Best Price Match
8.7 (63 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Free WiFi
Best Price Match Sedbury Farm Cottages Best Price Match
8.4 (156 Reviews) Apartment
Apartments • Free on-site parking • Free WiFi
Best Price Match Cabin Places to Stay in Chepstow
Over 5+ Cabin Places to Stay in or Near Chepstow
Parva Farmhouse Riverside Guesthouse Best Price Match
9.3 (657 Reviews) Country_house
Breakfast • Free on-site parking • Restaurant
Best Price Match 
Shepherd’s delight Best Price Match
9.6 (93 Reviews) Chalet
The entire place is yours • 15 m² size • Free on-site parking
Best Price Match 
Oak Tree Cabin Best Price Match
9.3 (70 Reviews) Camping
Free on-site parking • Pet friendly • Free WiFi
Best Price Match 
The Meadows Hut Best Price Match
9.4 (10 Reviews) Chalet
The entire place is yours • 15 m² size • Free on-site parking
Best Price Match 
Camp Hillcrest Horsebox Best Price Match
8.0 (25 Reviews) Tented_camp
Breakfast • Free on-site parking • Hot tub
Best Price Match Villa Places to Stay in Chepstow
Over 3+ Villa Places to Stay in or Near Chepstow
La Villa Olli -Natural pool & Jacuzzi Best Price Match
10.0 (7 Reviews) Villa
The entire place is yours • 279 m² size • Free on-site parking
Best Price Match 
Olli's Cottage-Terrace & Jacuzzi optional Best Price Match
9.7 (98 Reviews) Villa
The entire place is yours • 70 m² size • Free on-site parking
Best Price Match 
Olli's Summer House - Natural Pool & Jacuzzi optional Best Price Match
9.4 (9 Reviews) Villa
The entire place is yours • 150 m² size • Free on-site parking
Best Price Match Hotels in Chepstow
Over 19+ Hotels in or Near Chepstow
Two Rivers Lodge by Marston’s Inns Best Price Match
8.7 (1702 Reviews) Hotel
Breakfast • Free on-site parking • Restaurant
Best Price Match Delta Hotels by Marriott St Pierre Country Club Best Price Match
8.2 (2131 Reviews) Hotel
Breakfast • Free on-site parking • Indoor swimming pool
Best Price Match 
The Coach and Horses Inn Best Price Match
8.4 (659 Reviews) Bed_and_breakfast
Breakfast • Restaurant • Pet friendly
Best Price Match 
The Beaufort Hotel Best Price Match
7.7 (1614 Reviews) Hotel
Breakfast • Free on-site parking • Pet friendly
Best Price Match 
Parkfield (Chepstow BnB) Best Price Match
9.3 (440 Reviews) Bed_and_breakfast
Breakfast • Free on-site parking • Free WiFi
Best Price Match Castle View Hotel Best Price Match
7.2 (564 Reviews) Bed_and_breakfast
Breakfast • Pet friendly • Free WiFi
Best Price Match About Chepstow Vacation Rentals
Looking for places to stay in Chepstow? Compare top options in Monmouthshire.
With more than 36 Chepstow vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Chepstow.
Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Chepstow. Prices average US $188 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Chepstow, with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Stay Categories in Chepstow
Use These Quick Filters to Find a Vacation Rental in Chepstow
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Chepstow.
Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Chepstow. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.
Weather in Chepstow
Average temperatures and rainfall by month range to help plan your stay in Chepstow.
Mar - May
Avg High13°C / 55°F
Avg Low5°C / 41°F
Rainfall82 mm / 3.2 in
Jun - Aug
Avg High20°C / 68°F
Avg Low12°C / 54°F
Rainfall69 mm / 2.7 in
Sep - Nov
Avg High14°C / 57°F
Avg Low8°C / 46°F
Rainfall113 mm / 4.5 in
Dec - Feb
Avg High8°C / 46°F
Avg Low2°C / 36°F
Rainfall109 mm / 4.3 in