Gwynn holiday rentals

We found 128 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Gwynn that are perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and cable TV. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Gwynn

Showing deals for:25 Dec - 1 Jan

Property grounds
Property grounds
Exterior
Beach
Exceptional
(150 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
AU$6,145
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Living area
Property grounds
Interior
Room
Exceptional
(124 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

15% off
AU$1,572
for 7 nights, 1 room
AU$225 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
The pampas grass makes you feel like you are sitting at the ocean
Waterfront home with amazing views!
Dining Room table comfortably seats 10
Fully equipped Kitchen with stainless steel appliances
Exceptional
(69 reviews)

The Harbor House - Waterfront Home with Private Pier & Amazing Views!

Onemo

8% off
AU$3,316
for 7 nights, 1 home
AU$474 per night
includes taxes & fees
The Harbor House - Waterfront Home with Private Pier & Amazing Views!
Interior
Interior
Private kitchen
Interior
Exceptional
(11 reviews)

Beautiful Gwynn’s Island Waterfront Home

Gwynn

8% off
AU$3,934
for 7 nights, 1 home
AU$562 per night
includes taxes & fees
Beautiful Gwynn’s Island Waterfront Home
Master bed with sofa and views of Chesapeake Bay
Bahamas? in White Stone
Large open concept - perfect for entertaining!
Property grounds
Excellent
(20 reviews)

BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock

White Stone

10% off
AU$5,328
for 7 nights, 1 home
AU$761 per night
includes taxes & fees
BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock
Interior
Exterior detail
Interior
Interior
Exceptional
(47 reviews)

Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!

Gwynn

8% off
AU$3,247
for 7 nights, 1 home
AU$464 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Interior
Interior
Interior
Living area
Exceptional
(21 reviews)

Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home

Gwynn

8% off
AU$4,851
for 7 nights, 1 home
AU$693 per night
includes taxes & fees
Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Gwynn getaway

Enjoy the museums and other features of Gwynn. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Gwynn

Are you hoping to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Gwynn has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Golden Eagle Golf Club (13.1 mi / 21.1 km)
  • Compass Entertainment Complex (13.9 mi / 22.4 km)
  • Piankatank River Golf Club (10.7 mi / 17.2 km)
  • Gloucester Golf Club (15.3 mi / 24.6 km)

Exploring the natural features in Gwynn

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Gwynn is a great place to spend some time outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Bethel Beach Natural Area Preserve (7.3 mi / 11.8 km)
  • White Stone Beach (9.9 mi / 16 km)
  • Chesapeake Bay (10.3 mi / 16.6 km)
  • Holly Point Nature Park (3.2 mi / 5.2 km)
  • Bethel Beach (6.5 mi / 10.5 km)
  • Thousand Trails Beach Park (12.9 mi / 20.7 km)

How to get to and around Gwynn

The nearest airport is in Newport News, VA (PHF-Newport News - Williamsburg Intl.), located 28.5 mi (45.8 km) from the city centre.

Frequently asked questions

What is the best area to stay in Gwynn when booking a holiday rental?
When considering a holiday rental in Gwynn, Virginia, the best area to stay is along the picturesque coastline of the Chesapeake Bay. This region offers a tranquil escape, characterised by its stunning waterfront views and charming small-town atmosphere.The area boasts a variety of properties, from quaint cottages to larger homes, suiting different group sizes and preferences. Staying near the bay not only provides easy access to beautiful sandy beaches but also makes it convenient to explore local attractions such as the nearby historic sites and nature trails.One of the top attractions in the vicinity is the scenic Gwynn's Island, known for its serene beaches and opportunities for fishing and boating. Additionally, the nearby Mathews County Museum offers a fascinating glimpse into the area's history and culture, showcasing local artefacts and exhibits.
Where are the best areas for renting a beach house in Gwynn?
For renting a beach house in Gwynn, Virginia, the area around the Chesapeake Bay is particularly appealing. The community along the bay provides access to beautiful waterfront properties, many of which offer private docks, great for boating enthusiasts. These beach houses typically feature spacious decks for enjoying sunsets, outdoor grills for barbecues, and well-equipped kitchens for self-catering.In addition, properties located near Gwynn's local beaches, such as those by the nearby Mathews County, often come with amenities like private beach access, fire pits for evening gatherings, and ample outdoor space for activities like kayaking or paddleboarding. The serene environment around Gwynn is ideal for families and groups looking for a relaxing getaway, with many rentals also including charming interiors, comfortable furnishings, and modern conveniences like Wi-Fi and air conditioning.Moreover, the nearby historic waterfront towns provide opportunities for dining, shopping, and exploring local culture, making the region a delightful destination for beach house rentals.
What is the most popular type of holiday rental accomodation in Gwynn?
In Gwynn, holiday houses are the most popular type of holiday rental, with several available in the area. These properties typically offer spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and often outdoor spaces where guests can relax and enjoy the surrounding natural beauty. Additionally, mobile homes and cottages are also available, providing a range of options for travellers seeking a more unique or rustic experience. Cottages, in particular, tend to have charming interiors and may include amenities such as fireplaces and outdoor seating areas.
Are there any family house rentals in Gwynn?
In Gwynn, Virginia, there are some family-friendly house rentals available, with approximately ten options to choose from. This charming area offers a serene setting ideal for family gatherings, with many properties situated near the picturesque coastline of the Chesapeake Bay. Visitors can expect homes equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces great for children to play or for hosting barbecues.The locale is not far from attractions such as the nearby Mathews County, known for its quaint shops and local eateries, as well as the stunning natural beauty of the bay, providing opportunities for water activities like kayaking and fishing.
Are there pet-friendly house rentals in Gwynn?
In Gwynn, Virginia, there are several pet-friendly house rentals available, making it an excellent choice for travellers wishing to bring their furry companions along. Many of these holiday homes offer amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, ensuring a comfortable stay for both pets and their owners. The tranquil setting allows for peaceful retreats, and some properties may even feature private access to nearby natural attractions.While enjoying your stay, pet owners can explore the surrounding areas, which often include scenic spots great for walking and hiking with pets. The nearby natural beauty of the Chesapeake Bay and local parks enhances the experience, providing plenty of opportunities for outdoor activities.
Are there any remote work holiday rentals in Gwynn?
In Gwynn, Virginia, there are about 10 remote work-friendly holiday rentals available, making it a suitable destination for those looking to balance work and leisure. Many of these properties offer essential amenities such as free Wi-Fi, ensuring a reliable internet connection for remote work. Expect accommodations that provide comfortable living spaces, often with dedicated work areas, and additional features like fully equipped kitchens for convenient meal preparation.Nestled near the beautiful coastline and surrounded by scenic landscapes, Gwynn also provides opportunities for outdoor activities during downtime. Nearby attractions include charming local beaches and nature trails, great for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Gwynn?
In Gwynn, popular rental amenities include kitchens, allowing guests to prepare their own meals, and blenders for making smoothies or other refreshments. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the surrounding scenery. Additionally, rentals often come equipped with coffee and tea makers, ensuring that guests can start their day with a warm beverage. Paper towels are typically provided as well, adding to the convenience for travellers during their stay.
When is the best time to visit Gwynn for a holiday rental?
The peak season for visiting Gwynn, Virginia, runs from May to July, making it an ideal time for holiday rentals. With warm temperatures averaging between 20 to 30 degrees Celsius, this period is great for outdoor enthusiasts looking to explore the area's natural beauty. Whether you're hiking through scenic trails or enjoying water activities at the nearby Chesapeake Bay, the vibrant setting draws many travellers eager for adventure.July stands out as the most popular month, where you can immerse yourself in local events and enjoy the company of fellow visitors. The lively community vibe, combined with the beautiful summer weather, creates a fantastic backdrop for your holiday.For those mindful of budget, consider a visit in November. This month offers a quieter experience, allowing you to appreciate the fall's enchanting colours and the serene charm of Gwynn without the bustling crowds. The mild climate during this time, although cooler, can still be enjoyable for leisurely walks and exploring the local scenery.Ultimately, the best time to visit Gwynn depends on your preferences. If you thrive on the energy of summer activities and community events, the peak season is great for you. Alternatively, if you prefer a peaceful retreat amidst nature's beauty, the shoulder month of November could be your ideal choice.
What are the top attractions in Gwynn?
In Gwynn, Virginia, visitors can enjoy the natural beauty and outdoor activities that the area has to offer. The nearby Chesapeake Bay provides opportunities for fishing, boating, and enjoying scenic waterfront views. The Gwynn's Island is a popular spot for those looking to experience a quieter, more relaxed atmosphere, with its lovely beaches and nature trails.Additionally, the historic town of Mathews, just a short drive away, features charming shops and local eateries that showcase regional cuisine. The Mathews County Museum, also in the vicinity, offers insights into the local history and culture, making it a worthwhile stop for those interested in the area's heritage.For outdoor enthusiasts, the proximity to parks such as the nearby Bethel Beach Natural Area offers beautiful sandy shores and nature trails, ideal for hiking and birdwatching.
Are all fees included in the Gwynn holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Gwynn holiday homes with parking?
Stayz offers a wide selection of holiday homes in Gwynn with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Gwynn holiday homes?
You can find great discounts on holiday homes in Gwynn on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Gwynn holiday home booking on Stayz?
To find Gwynn holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Gwynn?
A long-stay holiday home in Gwynn is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Gwynn holiday home?
Book your Gwynn holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Gwynn?
Prices for holiday homes in Gwynn vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Gwynn to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.