Sister Bay Condo Rentals - Vacation Rentals in Chepstow Castle

The Potting Shed at Mathern Palace From US $186
         

10.0 (33 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Broadrock From US $155
         

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9.6 (19 Reviews)
Apartment
  • Parking
  • Balcony/Terrace
  • Security/Safety
Wallhope Retreat - Chepstow, spectacular views From US $313
         

10.0 (30 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • TV
New 3 Bedroom Flat Close to Station From US $163
         

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10.0 (8 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly
No.8 Accommodation From US $99
         

8.8 (55 Reviews)
Bed & Breakfast
  • Balcony/Terrace
  • Security/Safety
  • Guest Services
The Nook - Farm stay with hot tub - Chepstow From US $239
         

Wallhope Retreat From US $394
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Two Rivers, Chepstow by Marston’s Inns From US $167
         

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9.2 (414 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Charming 4-bedroom cottage in historic Chepstow From US $322
         

Clock Cottage - Luxury 2 bed Holiday Let From US $218
         

9.8 (32 Reviews)
Cottage
  • Parking
  • TV
  • Balcony/Terrace
The Potting Shed at Mathern Palace From US $244
         

9.0 (2 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • TV
The Elements Residence From US $1,205
         

New
House
  • Parking
  • Pet Friendly
  • TV
5 Bed in Chepstow (oc-h34098) From US $960
         

New
Cottage
  • Parking
  • Pet Friendly
  • Pool
2 bedroom accommodation in Chepstow From US $172
         

New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Premium 2BD Beaufort Square | Central Chepstow From US $150
         

Welsh Gatehouse: Historical Castle with EV Charger From US $257
         

Double or Twin Private Bathroom at No.8 Accommodation From US $132
         

9.8 (18 Reviews)
Hotel
  • TV
  • Balcony/Terrace
  • Security/Safety
Gardener’s Cottage at Mathern Palace - Chepstow From US $211
         

Spacious 3BR in Historic Chepstow, Cottage Garden From US $265
         

The Loft at BroadRock From US $139
         

5.0 (3 Reviews)
Apartment
  • TV
  • Balcony/Terrace
  • Bedding/Linens
Pro Tip: Sisterbaycondorentals makes it easy to compare the best listings on Sisterbaycondorentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sisterbaycondorentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chepstow Castle.

Weather in Chepstow Castle

View the weather forecast for Chepstow Castle before booking your Chepstow Castle 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

Chepstow Castle Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chepstow Castle?
How many vacation rentals are available in Chepstow Castle?

Currently, the total number of properties listed in 2026 is over 72 in the Chepstow Castle area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chepstow Castle.