Discover Your Perfect Chepstow Vacation Homes

Best Vacation Homes in Chepstow

Why Choose Rent By Owner for your Chepstow Vacation Rental Homes?

What makes our Vacation 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.

Popular Areas for Chepstow Vacation Rentals

Where are the best neighborhoods to stay in Chepstow?

When planning your stay in Chepstow, Newport, Rhode Island, choosing the right neighborhood can enhance your overall experience. The area offers a variety of charming communities, each with its own unique character and easy access to local attractions. Whether you prefer a quiet, residential setting or a lively district with vibrant amenities, you'll find suitable options nearby. Exploring different neighborhoods allows you to discover the perfect spot that complements your vacation style while enjoying the comfort and reliability of well-reviewed vacation rentals. With the right choice, your time in Newport will be both memorable and seamless from start to finish.

Cliff Walk

This scenic stretch along the coastline offers breathtaking ocean views and easy access to some of the region's most iconic sights, making it a perfect area for exploring on foot. Staying nearby ensures you can enjoy the natural beauty and vibrant atmosphere of Newport at your leisure.

View 1305+ Rentals in Cliff Walk

Wakefield-Peacedale

Known for its charming residential streets and local charm, this neighborhood provides a peaceful retreat while still being close to the region’s attractions. It’s an ideal choice if you seek a quiet stay with convenient access to coastal activities and unique dining options.

View 40+ Rentals in Wakefield-Peacedale

Ocean Drive

Famous for its stunning coastal scenery, Ocean Drive offers picturesque drives and access to beaches that showcase the area's maritime spirit. Here, you can enjoy the relaxed seaside ambiance and explore the scenic routes that define this destination.

View 90+ Rentals in Ocean Drive

Bonnet Shores

This beachside community is renowned for its sandy shores and vibrant summer scene, making it a popular spot for outdoor enthusiasts. Opting to stay in this area puts you close to pristine beaches and lively coastal activities.

View 111+ Rentals in Bonnet Shores

Easton's Point

With its historic charm and proximity to water, Easton's Point offers a quintessential coastal experience. It’s perfect for travelers looking to enjoy the area's maritime heritage and scenic landscapes while having easy access to the region’s amenities.

View 44+ Rentals in Easton's Point

Yachting Village

Centered around a bustling yacht scene, this neighborhood provides a luxurious waterfront atmosphere and plenty of opportunities for sailing and boating. Choosing to stay here connects you with the region’s rich maritime culture and upscale amenities.

View 299+ Rentals in Yachting Village

Snug Harbor

Nestled along the coast, Snug Harbor offers a tranquil setting with beautiful harbor views, making it an excellent base for maritime exploration. It's ideal for visitors seeking serenity combined with access to local water-based activities.

View 74+ Rentals in Snug Harbor

The Point

As one of the most historic neighborhoods, The Point boasts charming architecture and cobblestone streets that reflect the region’s rich past. Staying nearby provides a unique glimpse into the area's heritage and easy access to cultural attractions.

View 165+ Rentals in The Point

Best Times to Visit Chepstow

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as this destination offers different charms and activities depending on the season, making it essential to plan accordingly for a memorable stay in the area.

Peak Season Highlights

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Summer (June to August)

During the summer months, the region experiences warm weather that is ideal for exploring outdoor activities and enjoying the scenic coastal views. This season tends to attract visitors seeking a lively atmosphere in Chepstow, Newport, and nearby areas.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
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Fall (September to November)

The early fall season offers pleasant temperatures and beautiful foliage, making it a popular time for travelers looking to experience the area's natural beauty and local events. During this period, you can enjoy the region's vibrant autumn scenery.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Winter (December to February)

The winter months see fewer visitors as temperatures drop, providing a quieter experience with less crowded vacation rentals. This is an ideal time for cozy stays and exploring the region’s indoor attractions in a peaceful setting.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
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Early Spring (March to May)

Before the peak season begins, early spring offers mild weather and fewer tourists, allowing you to enjoy more relaxed visits. It’s a great time to find attractive deals on vacation rentals and explore at your own pace.

Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F

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

More Top-Rated Vacation Rentals in Chepstow Area

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 outdoor dining spaces, perfect for savoring meals while taking in the scenic views of the surrounding area.
  • Take advantage of private gardens or landscaped yards to relax or host gatherings during your stay.
  • Make use of outdoor grills and barbecue stations, ideal for casual cookouts in the region's pleasant climate.
  • Benefit from spacious patios or decks that offer a comfortable area to unwind outdoors.
  • Explore nearby walking trails or access outdoor recreation zones that are easily reachable from your rental.
  • Relish in access to outdoor swimming pools or hot tubs to enhance your relaxation experience.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars in this inviting destination.

Top Attractions Around Chepstow

What attractions are nearby?

Here, you can explore a variety of outdoor activities, scenic spots, and cultural attractions that highlight the charm of this destination and its surrounding region.

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Family Activities

  • Beavertail State Park: Explore scenic coastal views and enjoy family picnics at this popular park here, perfect for outdoor adventures with children.
  • The Newport Cliff Walk: Take a leisurely stroll along the rugged shoreline offering stunning ocean vistas, ideal for family outings in the region.
  • International Tennis Hall of Fame: Discover the history of tennis and participate in engaging exhibits that entertain visitors of all ages during your stay nearby.
  • Green Animals Topiary Garden: Wander through beautifully sculpted greenery, providing a unique outdoor experience that the entire family can appreciate here.
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Adult Activities

  • Chepstow Riverwalk: Take a leisurely stroll along the scenic riverwalk, enjoying views of the surrounding landscape and the historic bridge.
  • Newport Art Gallery: Explore the local art scene by visiting this gallery, which showcases contemporary and regional artworks designed to inspire.
  • Rhode Island Coastal Cruises: Embark on a relaxing boat tour that offers stunning views of the coastline and the chance to spot local wildlife.
  • Seaside Dining Experiences: Savor fresh seafood and regional cuisine at waterfront restaurants that capture the essence of coastal living here.

Chepstow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Markets: Take the opportunity to enjoy regional cuisine at local eateries and markets to truly savor the flavors of this coastal destination.
  • Plan Outdoor Activities: Make the most of the area's natural beauty by scheduling outdoor adventures like walking along scenic trails or relaxing by the waterfront.
  • Visit Nearby Historic Sites: Discover the region's rich history by setting aside time to explore historical landmarks and cultural attractions nearby.
  • Adjust Your Schedule for Seasonal Events: Check out seasonal festivals or events happening during your stay to experience the vibrant community spirit here.

Transportation Options

  • Car Rentals: Renting a car offers you the flexibility to explore this area and its surroundings at your own pace, with numerous local providers available nearby.
  • Public Transit: The regional bus services connect key points here, making it a convenient and budget-friendly transportation option for exploring the region.
  • Taxi Services: Taxis provide a reliable way to navigate the destination comfortably, especially for short trips or when traveling with luggage.
  • Bike Rentals: Biking is an eco-friendly and enjoyable way to discover the area's scenic spots and charming neighborhoods at a leisurely pace.

Local Customs Options

  • Clambakes and Seafood Traditions: You can embrace the local seafood culture by enjoying traditional clambakes, a cherished custom here that highlights the region’s maritime heritage.
  • Harbor Festivals: Participating in or simply observing these festivals offers insight into this destination’s strong connection to its nautical roots and community spirit.
  • Architectural Heritage: The area showcases historic architecture with colonial and maritime influences, reflecting the region's rich history and preservation efforts.
  • Community Autonomy Celebrations: Local events often celebrate the area's independent spirit, emphasizing its unique cultural identity within the broader Newport region.

Frequently Asked Questions About Chepstow?

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:

2. How many Rentbyowner vacation rentals are available in Chepstow?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1669 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. 

3. What is the cancellation policy for a vacation rental in Chepstow, Newport?

Cancellation policies vary by listing. To understand the specific terms and any applicable fees, please review the cancellation policy listed on the property details or contact the property owner directly.

4. How do I know if my preferred dates are available for booking in this region?

Availability depends on the individual property. You can check real-time availability by entering your desired dates on the listing page or reaching out to the host for confirmation.

5. Are there any additional fees or deposits required when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are specified in the listing details. For clarity, review these details carefully or contact the owner before finalizing your reservation.

6. What amenities can I expect at a vacation rental in this area?

Amenities vary across properties but often include essentials like Wi-Fi, parking, kitchen facilities, and laundry. For a complete list of amenities, consult the specific listing or contact the property owner directly.

7. What is the check-in and check-out process for here?

Check-in and check-out procedures are outlined in each listing, with many offering flexible options. To ensure a smooth experience, review the instructions provided or communicate directly with the host prior to your arrival.

Best Vacation Homes in Chepstow