Best Vacation Homes in Chepstow
Cottage
10.0(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
1281 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Pet Friendly
US $313/Night
7 Nights - US $2,188
House
10.0(37 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
US $186/Night
7 Nights - US $1,302
Cottage
10.0(6 Reviews)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Pet Friendly
Parking
Internet
US $311/Night
7 Nights - US $2,179
Cottage
10.0(21 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $165/Night
7 Nights - US $1,155
Apartment
10.0(8 Reviews)
3 Bedrooms
3 Baths
6 Guests
699.65 ft²
- Parking
- Internet
Child Friendly
Security/Safety
US $163/Night
7 Nights - US $1,140
Cottage
10.0(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
Kitchen- Parking
US $444/Night
7 Nights - US $3,111
Cottage
10.0(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $191/Night
7 Nights - US $1,336
Cottage
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $998
Chepstow Luxury Rentals
Cottage
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
Pool- Balcony/Terrace
US $1,355/Night
7 Nights - US $9,485
House
6 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,346/Night
7 Nights - US $9,425
House
10 Bedrooms
8 Baths
26 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,205/Night
7 Nights - US $8,437
US $994/Night
7 Nights - US $6,959
New
House
4 Bedrooms
2 Baths
9 Guests
322.92 ft²
- Hot Tub
- Fireplace/Heating
- View
- Parking
US $907/Night
7 Nights - US $6,351
House
8.6(7 Reviews)
7 Bedrooms
4 Baths
17 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $898/Night
7 Nights - US $6,288
House
9.8(6 Reviews)
7 Bedrooms
4 Baths
17 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $880/Night
7 Nights - US $6,157
Apartment
10 Bedrooms
8 Baths
22 Guests
2960.08 ft²
- View
- Parking
- Internet
- Child Friendly
US $671/Night
7 Nights - US $4,698
Chepstow Pet Friendly Vacation Rentals
Cabin
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
301 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $239/Night
7 Nights - US $1,671
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1280.91 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
US $394/Night
7 Nights - US $2,758
US $100/Night
7 Nights - US $703
Cottage
10.0(3 Reviews)
4 Bedrooms
1 Bath
7 Guests
1808 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $333/Night
7 Nights - US $2,330
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $218/Night
7 Nights - US $1,524
Cabin
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
162 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $177/Night
7 Nights - US $1,240
Cottage
Orchard holiday cottage is a beautiful romantic dwelling ideal for couples. This perfect property is
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $255/Night
7 Nights - US $1,784
Chepstow Large Vacation Homes
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
2300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $644/Night
7 Nights - US $4,511
House
9.5(48 Reviews)
5 Bedrooms
5 Baths
11 Guests
864.7 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
US $91/Night
7 Nights - US $640
Cottage
2.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
2314 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $472/Night
7 Nights - US $3,302
House
9.3(689 Reviews)
7 Bedrooms
7 Baths
14 Guests
172.22 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Breakfast
US $155/Night
7 Nights - US $1,085
Villa
7 Bedrooms
4 Baths
28 Guests
- Kitchen
- Internet
- Child Friendly
Laundry
US $1,949/Night
7 Nights - US $13,640
House
7 Bedrooms
4 Baths
28 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $1,838/Night
7 Nights - US $12,866
House
6 Bedrooms
3 Baths
14 Guests
3229 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,034/Night
7 Nights - US $7,241
US $959/Night
7 Nights - US $6,713
Why Choose Rent By Owner for your Chepstow Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 Vacation Rentals stay?
Timing your visit to this charming region can greatly enhance your experience, so consider the local climate and seasonal events to choose the perfect moment for your stay in Chepstow, United Kingdom.
Peak Season Highlights
Summer (June to August)
During the warmest months, you’ll enjoy longer days and generally pleasant weather, making it ideal for exploring the surrounding countryside and enjoying outdoor activities in this region.
Average Temperature Daytime: 18-22°C - Nighttime: 12-15°C
Spring (March to May)
This vibrant season offers mild weather and blooming landscapes that enhance your stay here, perfect for sightseeing and outdoor adventures with a touch of natural beauty.
Average Temperature Daytime: 11-16°C - Nighttime: 6-10°C
Off-Season Highlights
Autumn (September to November)
As the region transitions into cooler temperatures, fewer visitors mean a peaceful atmosphere, ideal for those seeking tranquility and scenic views during your getaway.
Average Temperature Daytime: 14-19°C - Nighttime: 8-12°C
Winter (December to February)
Respite from peak crowds, winter here offers a quiet retreat with crisp air and short daylight hours, suitable for cozy stays and reflective exploration.
Average Temperature Daytime: 7-10°C - Nighttime: 2-5°C
Weekly Weather Forecast for Chepstow
How to Book Your Chepstow Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Chepstow
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 spacious outdoor seating areas perfect for relaxing or dining al fresco amidst the scenic surroundings.
- Take advantage of private gardens or lawns that offer a peaceful retreat in this charming region.
- Make use of outdoor play equipment, ideal for families traveling with children in this picturesque destination.
- Gather around an outdoor fireplace or fire pit to unwind and share stories after a day exploring the area.
- Benefit from access to walking trails or paths directly from your rental for scenic hikes in the countryside.
- Utilize dedicated outdoor dining spaces designed for enjoying meals while soaking up the natural beauty of this location.
- Indulge in outdoor recreational amenities such as bikes, kayaks, or fishing gear available at select properties here.
Top Attractions Around Chepstow
What attractions are nearby?
While staying in this region, you can enjoy a variety of outdoor activities and explore local sites that showcase the area's rich history and natural beauty.
Family Activities
- Chepstow Castle: Explore this historic castle that offers captivating views and interactive exhibits, perfect for family adventures in the region.
- The National Dive & Activity Centre: Discover an array of water-based activities, such as kayaking and climbing, designed to keep the whole family engaged and active nearby.
- Total Adrenaline: Experience high-energy indoor activities like laser tag and trampolining, ideal for families seeking fun and excitement here.
- Severn View Services: Enjoy scenic picnic spots and family-friendly amenities along the river, providing a relaxing way to appreciate the area's natural beauty.
Adult Activities
- Chepstow Castle Tour: Explore the historic ruins of this impressive Norman castle, offering a glimpse into the region’s medieval past and stunning views of the Wye Valley.
- The Wye Valley Walk: Embark on a scenic hike along the Wye Valley, where lush landscapes and river vistas provide a perfect setting for outdoor enthusiasts staying in the area.
- Severn Bridge Experience: Visit the iconic Severn Bridge, which offers breathtaking panoramic views and an opportunity to appreciate the engineering marvel connecting this destination to nearby regions.
- Monmouthshire & Brecon Canal Boat Trip: Enjoy a leisurely boat ride along the canal, immersing yourself in tranquil waterscapes while discovering the natural beauty of the surrounding countryside.
Other Places to Stay in Chepstow
Llanvair Discoed
Tintern Abbey
Symonds Yat Rock
Chepstow Museum
Parva Farm Vineyard
Chepstow Castle
Tidenham
Chepstow Racecourse
Trelleck Grange
Tintern
Gate House
Mathern
Chepstow Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local history: Take time to visit historic sites and landmarks nearby to truly appreciate the rich heritage that makes this destination unique.
- Discover scenic walks: Enjoy the area's natural beauty by strolling along well-known trails and pathways, which offer stunning views and memorable experiences.
- Sample regional cuisine: Dine at local eateries to indulge in authentic flavors that showcase the region's culinary traditions.
- Plan day trips: Use your stay as a base to explore neighboring attractions and destinations, enhancing your overall experience here.
Transportation Options
- Chepstow Railway Station: This station offers convenient train services connecting you to major cities and surrounding regions, making it easy to explore the area and beyond.
- Bus Services in Chepstow: Local bus routes provide affordable and frequent transportation options for navigating throughout the town and nearby attractions.
- Taxis and Private Hire Vehicles: Available readily within the region, taxis offer a flexible way to travel directly from your vacation rental to key destinations or the train station.
- Car Rentals: Renting a vehicle here allows you to enjoy the scenic surroundings at your own pace, with numerous rental agencies available nearby for your convenience.
Local Customs Options
- Local Lords and the Chepstow Castle Heritage: You can immerse yourself in the region’s history by understanding the significance of local lords who once governed this area, reflected today through the iconic Chepstow Castle.
- The Wye Valley Fairy Traditions: In this destination, local folklore and fairy traditions remain a cherished part of the culture, adding a mystical charm to your experience here.
- Weekly Market Customs: Visitors often observe the traditional weekly markets that continue to serve as social hubs, showcasing regional produce and crafts in the heart of the town.
- River Etiquette and Waterway Respect: Here, respecting the Wye River through local customs is important, especially during recreational activities, emphasizing the community’s reverence for this natural resource.
Chepstow Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Chepstow?
There are a lot of options in Chepstow. If you plan on staying in the Chepstow area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chepstow:
- The Potting Shed at Mathern Palace
- Wallhope Retreat - Chepstow, spectacular views
- Cider Mill Lodge - HW7420
- Welsh Marches - Sugar Loaf
- 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
- Pet friendly 'Home from Home in the Wye Valley Wales
2. Which vacation homes in Chepstow are best for families?
If you are looking for a family-friendly vacation home in Chepstow, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chepstow:
3. How many Rentbyowner vacation rentals are available in Chepstow?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 124 in the Chepstow area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chepstow.
4. What is the cancellation policy for vacation rentals in Chepstow?
Cancellation policies vary depending on the individual property listing. You should review the specific rental's cancellation terms before booking, as they are detailed in the listing or can be confirmed by contacting the property owner directly.
5. How do I find available dates and book a vacation rental in Chepstow?
You can check the availability calendar on the listing page and follow the booking process to reserve your stay. For precise availability and to secure your reservation, it’s best to contact the property owner if you have specific dates in mind.
6. Are there any additional fees or charges for staying in a vacation rental here?
Additional fees such as cleaning charges, security deposits, or service fees are typically outlined in each property listing. To ensure transparency, review all costs associated with your chosen rental before completing your booking.
7. What amenities are typically included with vacation rentals in Chepstow?
Most rentals in the area offer essential amenities like Wi-Fi, parking, and fully equipped kitchens. However, exact amenities vary between properties, so reviewing the listing details will give you a complete understanding of what is provided.
8. How do I contact the property owner if I have questions about my stay?
You can reach out to the property owner through the messaging feature on the listing platform. This allows you to clarify details about your stay, ask about special requests, or confirm any specific requirements before booking.
Chepstow Top Rated Vacation Rentals
Hotel
8.2(1006 Reviews)
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $127/Night
7 Nights - US $890
Hotel
8.1(2130 Reviews)
8 Baths
326.95 ft²
Private Pool- Hot Tub
- Spa
- Fireplace/Heating
US $149/Night
7 Nights - US $1,042
Cottage
5 Bedrooms
4 Baths
10 Guests
1722 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $828/Night
7 Nights - US $5,796
