Discover Your Perfect Chepstowe Vacation Homes

Best Vacation Homes in Chepstowe

Cottage
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like-icon10.0
Exceptional
(89 Reviews)
1 Bedroom 1 Bath 4 Guests 775 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $171/Night 7 Nights - US $1,200
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House
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like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 4 Guests 1291.67 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $227/Night 7 Nights - US $1,592
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Cottage
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like-icon9.0
Exceptional
(105 Reviews)
1 Bedroom 1 Bath
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $126/Night 7 Nights - US $879
House
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like-icon10.0
Exceptional
(8 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Internet
    Internet
  • Child Friendly
    Child Friendly
More amenities
US $179/Night 7 Nights - US $1,253
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House
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like-icon9.9
Exceptional
(32 Reviews)
1 Bedroom 1 Bath 2 Guests 150.69 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
More amenities
US $173/Night 7 Nights - US $1,210
House
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like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 2 Guests 155 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $137/Night 7 Nights - US $961
House
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like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $272/Night 7 Nights - US $1,904
House
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like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $175/Night 7 Nights - US $1,222

Chepstowe Luxury Rentals

Other
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10 Bedrooms 1 Bath 1 Guest 645.83 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $1,620/Night 7 Nights - US $11,338
House
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13 Bedrooms 6 Baths 42 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $1,540/Night 7 Nights - US $10,783
New
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House
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3 Bedrooms 1 Bath 5 Guests 1453.13 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $1,071/Night 7 Nights - US $7,495
Villa
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3 Bedrooms 3 Baths 6 Guests 2799 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $837/Night 7 Nights - US $5,860
House
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like-icon9.4
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $590/Night 7 Nights - US $4,132
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House
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like-icon7.7
Very Good
(3 Reviews)
4 Bedrooms 2 Baths 8 Guests 3046.19 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
US $558/Night 7 Nights - US $3,907
House
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like-icon9.6
Exceptional
(15 Reviews)
8 Bedrooms 4 Baths 22 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $509/Night 7 Nights - US $3,565
Villa
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1 Bedroom 1 Bath 3 Guests 1723 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $486/Night 7 Nights - US $3,405

Chepstowe Pet Friendly Vacation Rentals

House
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2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $181/Night 7 Nights - US $1,266
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House
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like-icon9.5
Exceptional
(11 Reviews)
1 Bedroom 1 Bath 2 Guests 139.93 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $158/Night 7 Nights - US $1,109
House
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1 Bedroom 1 Bath 2 Guests 139 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $137/Night 7 Nights - US $961
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Apartment
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like-icon9.5
Exceptional
(2 Reviews)
1 Bedroom 2 Baths 8 Guests 3229.17 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $205/Night 7 Nights - US $1,438
House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $141/Night 7 Nights - US $990
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
5 Bedrooms 3 Baths 10 Guests 2153 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $277/Night 7 Nights - US $1,937
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 8 Guests
  • Pet Friendly
    Pet Friendly
  • Child Friendly
    Child Friendly
More amenities
US $265/Night 7 Nights - US $1,857
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $230/Night 7 Nights - US $1,607

Chepstowe Large Vacation Homes

House
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like-icon9.8
Exceptional
(103 Reviews)
5 Bedrooms 2 Baths 15 Guests 3122 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $264/Night 7 Nights - US $1,849
House
Map-icon
like-icon9.0
Exceptional
(1 Review)
1 Bedroom 3 Baths 10 Guests 2152.78 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $303/Night 7 Nights - US $2,123
House
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5 Bedrooms 2 Baths 18 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $373/Night 7 Nights - US $2,610
Villa
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4 Bedrooms 4 Baths 8 Guests 7319.46 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
US $315/Night 7 Nights - US $2,207
Other
Map-icon
like-icon10.0
Exceptional
(1 Review)
10 Bedrooms 6 Baths 23 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $850/Night 7 Nights - US $5,949
House
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like-icon5.0
Average
(26 Reviews)
5 Bedrooms 3 Baths 12 Guests
  • Child Friendly
    Child Friendly
US $612/Night 7 Nights - US $4,284
House
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5 Bedrooms 3 Baths 10 Guests 38 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $941/Night 7 Nights - US $6,587
House
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5 Bedrooms 3 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $664/Night 7 Nights - US $4,646

Why Choose Rent By Owner for your Chepstowe 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.

Best Times to Visit Chepstowe

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as seasonal weather patterns in this region influence the best periods for enjoying its natural beauty and local activities.

Peak Season Highlights

spring
Spring (September to November)

During the spring months, you can enjoy pleasant weather and vibrant landscapes, making it an ideal time for exploring this destination while staying in well-appointed vacation rentals.

Average Temperature Daytime: 15-22°C - Nighttime: 7-12°C
summer
Summer (December to February)

The summer season offers warmest temperatures and longer days, perfect for outdoor activities and experiencing the region's natural beauty from comfortable vacation rentals.

Average Temperature Daytime: 24-30°C - Nighttime: 14-17°C

Off-Season Highlights

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Autumn (March to May)

In autumn, the area's scenery transforms with colorful foliage, providing a peaceful setting to enjoy your stay in quiet and cozy vacation rentals.

Average Temperature Daytime: 13-20°C - Nighttime: 6-10°C
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Winter (June to August)

The winter months bring cooler weather and fewer visitors, offering a tranquil atmosphere that allows you to savor the beauty of this destination in relaxed vacation rentals.

Average Temperature Daytime: 8-14°C - Nighttime: 2-5°C

Weekly Weather Forecast for Chepstowe

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 the outdoors with a private outdoor dining area, perfect for meals amidst scenic views of the region.
  • Make the most of your stay with access to a spacious backyard or garden space, ideal for relaxing or outdoor activities.
  • Take advantage of a barbecue grill setup, allowing you to indulge in outdoor cooking and social gatherings.
  • Relax on a shaded patio or verandah, offering a comfortable spot to unwind while soaking in the natural surroundings.
  • Utilize outdoor recreational equipment such as bikes, kayaks, or fishing gear, available for exploring the nearby landscape.
  • Benefit from landscaped gardens or lawns that provide a lush environment for outdoor play or quiet reflection.
  • Some properties may feature a pool or hot tub, offering a luxurious way to cool off or relax after exploring this destination's scenic areas.
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Family Activities

  • Chepstowe Riverside Park: Enjoy a family picnic and leisurely stroll along the peaceful riverfront in this scenic local park.
  • Historic Chepstowe Lookout: Take in panoramic views of the surrounding countryside while exploring a site rich in local history and natural beauty.
  • Nature Trails around Chepstowe: Discover easy-to-navigate walking paths perfect for family outings and observing native flora and fauna.
  • Local Farmers Market: Experience the region’s fresh produce and handmade crafts, ideal for a relaxed family morning in this charming setting.
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Adult Activities

  • Exploring the Wineries: Sample local wines at renowned vineyards in the area, experiencing the region's rich viticultural heritage firsthand.
  • Hiking and Nature Walks: Discover scenic trails through lush landscapes and enjoy panoramic views unique to this destination’s natural surroundings.
  • Visiting Historic Sites: Delve into the area's history by exploring preserved landmarks that tell the story of the region’s past.
  • Golfing: Play a round at nearby golf courses designed for both leisure and advanced players, set against picturesque scenery.

Chepstowe Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine and Wineries: Take the time to sample the region’s renowned local produce and visit nearby wineries to enhance your authentic experience here.
  • Plan Outdoor Activities: Make the most of the area's natural beauty by organizing outdoor adventures like hiking, cycling, or nature walks during your stay.
  • Discover Hidden Gems: Ask locals or do some research to uncover lesser-known spots that offer unique views and a quieter atmosphere in this destination.
  • Book Flexible Accommodation Solutions: Choose well-equipped vacation rentals that provide comfort and flexibility, ensuring a relaxing and seamless visit to the region.

Transportation Options

  • Chepstowe Bus Service: Local bus routes connect you to surrounding towns and regional centers, making it easy to explore the area without a car.
  • Regional Train Services: The nearby railway stations offer convenient train options for traveling further across Victoria, ideal for day trips or commuting.
  • Car Hire Services: Numerous car rental agencies operate here, providing flexible transportation choices to visit remote attractions or enjoy scenic drives.
  • Taxi and Rideshare Options: Available throughout the region, these services offer quick and reliable transportation for your local travels around Chepstowe and beyond.

Local Customs Options

  • Welcome to the Local Wattle Ceremony: During your stay, you might observe this region's traditional practice of welcoming visitors with a display of native wattle branches, symbolizing unity and respect.
  • Participating in the Anzac Commemoration: The area observes a memorial service honoring the Anzac soldiers, highlighting the community’s deep connection to Australian history and patriotism.
  • Respect for Indigenous Heritage: You will notice that local customs often include acknowledging the traditional custodians of the land, fostering awareness and respect for Aboriginal culture here.
  • Celebration of the Harvest Festival: Celebrated annually, this community event showcases regional produce and celebrates the area's agricultural roots, providing an authentic cultural experience during your visit.

Frequently Asked Questions About Chepstowe?

2. How many vacation rentals have private pools in Chepstowe?

There are 1 vacation rentals with private pools near Chepstowe. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chepstowe are best for families?

If you are looking for a family-friendly vacation home in Chepstowe, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chepstowe:

4. How many Rentbyowner vacation rentals are available in Chepstowe?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 138 in the Chepstowe 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 Chepstowe. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies depending on the property owner. You should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancellations.

6. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning charges, service fees, or security deposits may apply. These will be outlined in the property listing, so it’s advisable to read all the details or reach out to the owner for clarification.

7. How can I ensure my reservation is confirmed and secure?

To secure your booking, follow the platform’s reservation process and verify that your payment has been processed successfully. Confirmations are typically sent via email, but contacting the property owner can provide extra reassurance.

8. What amenities are typically included in vacation rentals in this region?

Most vacation rentals here include essential amenities such as Wi-Fi, fully equipped kitchens, and parking. For specific features like pools or outdoor spaces, check each listing’s details or contact the owner directly.

9. Is it possible to modify or extend my stay after booking?

Modifications or extensions depend on the property's availability and the owner's policies. Contact the owner directly through the platform to discuss possible changes to your reservation.

Chepstowe Top Rated Vacation Rentals

House
Map-icon
like-icon9.2
Exceptional
(17 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $214/Night 7 Nights - US $1,501
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Hotel
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like-icon8.6
Fabulous
(531 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $87/Night 7 Nights - US $608
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Hotel
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like-icon8.4
Excellent
(793 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $91/Night 7 Nights - US $639
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Hotel
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like-icon8.3
Excellent
(365 Reviews)
5 Baths 284.17 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $87/Night 7 Nights - US $612
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Hotel
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like-icon8.2
Excellent
(1464 Reviews)
6 Baths 245.78 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $74/Night 7 Nights - US $518
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Hotel
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like-icon8.2
Excellent
(1449 Reviews)
6 Baths 339.06 ft²
  • Private Pool
    Private Pool
  • Spa
    Spa
More amenities
US $105/Night 7 Nights - US $732
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Hotel
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like-icon8.2
Excellent
(429 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $83/Night 7 Nights - US $582
Hotel
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like-icon7.4
Very Good
(635 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $79/Night 7 Nights - US $553