Chester Shores holiday rentals
We found 28 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Chester Shores to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chester Shores

Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!
Sleeps 9 · 4 bedrooms · 2 bathrooms

Serene Loon Lake Waterfront - Sleeps up to 10
Sleeps 10 · 4 bedrooms · 2+ bathrooms

Loon Lake, Chestertown - close to Gore: cozy, clean and bright chalet for 6-8
Sleeps 8 · 4 bedrooms · 2+ bathrooms

Private Lake Front Adirondack Retreat on Loon Lake-20 Min from Lake George, Gore
Sleeps 8 · 3 bedrooms · 1+ bathroom

Loon Lake Chalet with HOT TUB,kayaks, canoe, Close to Gore Mnt and Lake George
Sleeps 8 · 3 bedrooms · 3 bathrooms

4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.
Sleeps 10 · 4 bedrooms · 2 bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
When is the best time to visit Chester Shores for a holiday rental?
The peak season for visiting Chester Shores falls between June and August, with July being the most popular month for holiday rentals. During this vibrant period, the area comes alive with visitors eager to enjoy the beautiful beaches, water sports, and the warm summer weather, great for outdoor fun. With temperatures typically ranging from 20 to 30 degrees Celsius, you can expect plenty of sunshine, ideal for sunbathing, swimming, or exploring the scenic shoreline.If you prefer a quieter experience and are looking for good value, consider planning your trip in November. This month offers a peaceful atmosphere where you can enjoy the natural beauty of Chester Shores without the summer crowds. Although the weather is cooler, you can still appreciate the area's charm and take leisurely walks along the coast, making it a lovely time for reflection and relaxation.Ultimately, your choice will depend on whether you wish to immerse yourself in the bustling summer vibe or enjoy the tranquillity of the off-peak season.
What are the top attractions in Chester Shores, New York, United States of America?
In Chester Shores, visitors can enjoy a tranquil setting with a focus on outdoor activities. The nearby Chester Town Park provides scenic views and walking trails, great for leisurely strolls or picnics. The area is also known for its access to various lakes, offering opportunities for fishing and kayaking.For those interested in local culture, the charming town centre features quaint shops and eateries that reflect the community's character. While the neighbourhood is primarily residential, its proximity to larger towns means attractions such as the historic sites and vibrant dining options in nearby areas can be easily reached.
Are all fees included in the Chester Shores 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 Chester Shores holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chester Shores 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 Chester Shores holiday homes?
You can find great discounts on holiday homes in Chester Shores 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 Chester Shores holiday home booking on Stayz?
To find Chester Shores 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 Chester Shores?
A long-stay holiday home in Chester Shores 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 Chester Shores holiday home?
Book your Chester Shores 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 Chester Shores?
Prices for holiday homes in Chester Shores 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 Chester Shores 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.
