Chepstow Cottage Rentals

10.0 (21 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
10.0 (10 Reviews)
Cottage
  • Pet Friendly
  • TV
  • Balcony/Terrace

Why Choose Rent By Owner for your Chepstow Cottage Rentals?

What makes our Cottage Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chepstow

When should you plan your Cottage Rentals stay?

To make the most of your stay in this charming destination, consider visiting during the shoulder seasons when the region offers a peaceful atmosphere and moderate weather, ensuring a comfortable and enjoyable holiday experience in the area.

Peak Season Highlights

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Summer (June to August)

During the summer months, this region experiences warm weather and longer daylight hours, making it ideal for outdoor activities and exploring the scenic countryside.

Average Temperature Daytime: 20-25°C - Nighttime: 13-17°C
spring
Spring (March to May)

Spring brings a burst of color and mild temperatures, perfect for enjoying the natural beauty and tranquility of the area.

Average Temperature Daytime: 12-18°C - Nighttime: 6-10°C

Off-Season Highlights

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Autumn (September to November)

As the leaves change color, the region offers a quieter atmosphere, allowing you to experience its landscapes with fewer visitors.

Average Temperature Daytime: 14-19°C - Nighttime: 8-12°C
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Winter (December to February)

The colder months bring a peaceful charm, ideal for those seeking a cozy retreat away from the crowds.

Average Temperature Daytime: 7-10°C - Nighttime: 2-5°C

Weekly Weather Forecast for Chepstow

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for meals amidst picturesque scenery.
  • Relax in your own private garden or landscaped yard designed for outdoor leisure.
  • Take advantage of nearby walking trails and scenic routes to explore the area's natural beauty.
  • Make use of a spacious patio or terrace for entertaining guests or just unwinding.
  • Benefit from access to outdoor sports facilities like tennis courts or golf courses in the region.
  • Spend time in outdoor fire pits or barbecue setups, ideal for cozy evenings.
  • Experience the tranquility of outdoor seating areas that invite you to enjoy the surrounding countryside.
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Family Activities

  • Chepstow Castle: Explore this historic fortress that offers engaging tours and spectacular views, making it a perfect family outing in the area.
  • The National Diving & Conference Centre: Discover exciting water activities and indoor diving experiences suitable for children and teenagers alike.
  • Chepstow Racecourse: Attend lively race events that provide fun-filled entertainment for the whole family amidst picturesque surroundings.
  • The Wye Valley: Enjoy scenic walks, nature trails, and outdoor adventures along this stunning river valley that's ideal for family exploration and picnics.
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Adult Activities

  • Chepstow Castle Tour: Explore the historic Chepstow castle and immerse yourself in centuries of local history and architecture.
  • Wye Valley Walks: Enjoy scenic strolls along the picturesque Wye Valley, known for its stunning landscapes and tranquil atmosphere.
  • Local Craft Breweries: Sample regional flavors at nearby craft breweries, perfect for savoring unique ales and socializing.
  • The National Diving & Activity Centre: Experience adventurous water activities on this renowned site, ideal for exhilarating days out in the nearby region.

Other Places to Stay in Chepstow

Llanvair Discoed
Tintern Abbey
Symonds Yat Rock
Chepstow Museum
Parva Farm Vineyard
Chepstow Castle
Chepstow Racecourse
Trelleck Grange

Chepstow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local historic sites: Take time to visit the area's renowned historic landmarks for a deeper appreciation of its rich heritage and unique charm.
  • Enjoy scenic outdoor activities: Make the most of the region's natural beauty by engaging in walking trails or outdoor excursions that showcase the landscape's best features.
  • Visit nearby markets and eateries: Immerse yourself in the local culture by exploring markets and dining establishments that highlight regional flavors.
  • Plan your stay around seasonal events: Check the calendar for festivals or community events, ensuring your visit coincides with vibrant celebrations in this destination.

Transportation Options

  • Chepstow Railway Station: This station provides convenient rail connections to major cities, making it easy for you to explore the surrounding region when staying in your chosen cottages.
  • Local Bus Services: Regular bus routes operate throughout the area, offering affordable and flexible transportation options to nearby towns and attractions.
  • Taxis and Private Hire Vehicles: Availability of taxis allows for quick, personalized transport around Chepstow and its surroundings, ideal for short trips or last-minute plans.
  • Car Rentals: Numerous car rental agencies serve the region, giving you the freedom to explore at your own pace while enjoying the comfort of your cottage accommodation.

Local Customs Options

  • Welsh Hospitality: Visitors often notice the warm and welcoming attitude of locals, reflecting the region's deep-rooted tradition of friendliness and community spirit.
  • Traditional Pubs: Exploring local pubs offers a glimpse into the area's customs, where sharing stories over locally brewed ales is a cherished pastime.
  • Festivals and Fairs: Participating in regional festivals provides an authentic experience of local customs, showcasing traditional music, dance, and crafts unique to this destination.
  • Historic Celebrations: Engaging in annual celebrations preserves centuries-old traditions that continue to shape the cultural identity of this part of the United Kingdom.

Frequently Asked Questions About Chepstow Rental Cottages

1. What are the top Cottages in Chepstow?

2. How many Cottages are available in Chepstow?

Currently, the total number of properties listed by RBO in 2026 is over 41 in the Chepstow area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Chepstow. 

3. What is the cancellation policy for cottages in Chepstow, United Kingdom?

Cancellation policies vary depending on the specific listing. To find detailed information about your booking's cancellation terms, please refer to the listing details or contact the property owner directly.

4. Are there any specific check-in and check-out times I should be aware of when staying in a cottage here?

Check-in and check-out times are set by individual owners. For precise timings and any special instructions, review the property listing or communicate directly with the host prior to your arrival.

5. Is there a secure deposit required when booking a cottage in this area?

Many properties may require a security deposit, which is typically refundable upon a satisfactory inspection after your stay. Details about deposits are provided in the listing, so please read the description carefully or ask the owner for clarification.

6. Can I bring pets to cottages in Chepstow, United Kingdom?

Pet policies differ among listings. Some cottages welcome pets, while others do not. For specific information, check the property description or contact the owner to confirm whether your furry friends are permitted.

7. What amenities are typically included in cottages here to ensure a comfortable stay?

Amenities vary but often include essentials like Wi-Fi, kitchen facilities, and parking. To ensure the property meets your needs, review the amenities listed on the property page or reach out to the owner for additional details.

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