Best Vacation Homes in Chester
Apartment
10.0(56 Reviews)
2 Bedrooms
1 Bath
6 Guests
1250 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $215/Night
7 Nights - US $1,505
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
9149.32 ft²
Pool
Pet Friendly- Parking
Air Conditioner
US $309/Night
7 Nights - US $2,163
Hotel
8.6(1003 Reviews)
1 Bath
- Pool
Breakfast- Kitchen
- Parking
US $130/Night
7 Nights - US $910
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $211/Night
7 Nights - US $1,480
Apartment
9.2(5 Reviews)
1 Bedroom
1 Bath
2 Guests
View- Parking
- Air Conditioner
Internet
US $213/Night
7 Nights - US $1,491
House
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $269/Night
7 Nights - US $1,884
Apartment
9.8(8 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $197/Night
7 Nights - US $1,378
House
9.6(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $204/Night
7 Nights - US $1,425
Chester Luxury Rentals
Villa
10 Bedrooms
5 Baths
25 Guests
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $3,182/Night
7 Nights - US $22,276
House
10.0(19 Reviews)
10 Bedrooms
5 Baths
25 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,606/Night
7 Nights - US $18,245
New
Villa
11 Bedrooms
4 Baths
28 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,160/Night
7 Nights - US $15,119
Villa
9 Bedrooms
5 Baths
28 Guests
4499.31 ft²
Oceanfront- Hot Tub
- Fireplace/Heating
- Pool
US $1,992/Night
7 Nights - US $13,941
Villa
9.6(14 Reviews)
7 Bedrooms
5 Baths
16 Guests
4700 ft²
- Private Pool
- Fireplace/Heating
- Pool
Ocean View
US $1,763/Night
7 Nights - US $12,340
House
9.0(2 Reviews)
7 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,494/Night
7 Nights - US $10,456
House
9.8(18 Reviews)
7 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $931/Night
7 Nights - US $6,516
Apartment
4 Bedrooms
2 Baths
10 Guests
5005.22 ft²
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
US $894/Night
7 Nights - US $6,258
Chester Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $242/Night
7 Nights - US $1,694
Villa
5 Bedrooms
3 Baths
17 Guests
2798.62 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $789/Night
7 Nights - US $5,526
Villa
9 Bedrooms
4 Baths
25 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,833/Night
7 Nights - US $12,834
House
10.0(32 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $733/Night
7 Nights - US $5,130
House
7.4(3 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $699/Night
7 Nights - US $4,894
House
5 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $887/Night
7 Nights - US $6,207
House
10.0(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
Spa- Fireplace/Heating
- Ocean View
US $1,000/Night
7 Nights - US $7,000
House
10.0(1 Review)
5 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $697/Night
7 Nights - US $4,876
Chester Large Vacation Homes
Villa
8.8(9 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $803/Night
7 Nights - US $5,618
House
8.6(4 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $267/Night
7 Nights - US $1,869
House
5 Bedrooms
2 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $627/Night
7 Nights - US $4,389
US $2,413/Night
7 Nights - US $16,893
House
10.0(1 Review)
5 Bedrooms
4 Baths
15 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $765/Night
7 Nights - US $5,355
House
9.0(2 Reviews)
5 Bedrooms
3 Baths
9 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $540/Night
7 Nights - US $3,782
House
8.8(30 Reviews)
6 Bedrooms
4 Baths
14 Guests
5500 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $1,198/Night
7 Nights - US $8,383
House
7.4(3 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,075/Night
7 Nights - US $7,528
Why Choose Rent By Owner for your Chester 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 Chester
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you experience its best weather and local events, making your stay here truly memorable and helping you select the perfect vacation rentals for your getaway.
Peak Season Highlights
Summer (June to August)
During the warmer months, this destination experiences peak visitation due to its pleasant weather and outdoor activities.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn attracts travelers with its vibrant foliage and comfortable temperatures, making it an ideal time for outdoor exploration.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Late Winter (January to February)
The quieter winter period offers a peaceful environment for those seeking solitude and off-season savings.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Early Spring (March to May)
Early spring sees fewer visitors, providing an excellent opportunity to enjoy the area’s natural beauty without crowds.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Chester
How to Book Your Chester 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 Chester
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 seating areas like patios or decks to relax and take in the scenic views of the region.
- Take advantage of private or shared gardens to immerse yourself in the natural beauty surrounding your stay.
- Make use of outdoor grills for barbecuing and outdoor dining experiences amid the area's fresh air.
- Benefit from access to a swimming pool or hot tub to unwind after exploring the local attractions.
- Explore spacious yards or lawns perfect for outdoor activities, games, or simply unwinding outdoors.
- Utilize nearby walking trails or nature paths accessible directly from your rental property.
- Access covered porches or verandas ideal for enjoying morning coffee while soaking in the peaceful atmosphere here.
Top Attractions Around Chester
What attractions are nearby?
Discover a variety of outdoor activities and local attractions nearby, offering you the perfect opportunity to explore the natural beauty and charming scenery of this destination.
Family Activities
- Hudson Highlands Nature Museum: Engaging with the natural world through interactive exhibits and outdoor trails offers your family a fun-filled day immersed in the region's scenic beauty.
- Albert Wisner Public Library: Participating in children's storytimes and educational programs at the local library ensures a delightful, enriching outing for the whole family.
- Chester Farmers Market: Visiting the farmers market allows you to taste fresh local produce and crafts, fostering a vibrant community experience in this destination.
Adult Activities
- Hudson Highlands State Park: Explore scenic hiking trails and enjoy breathtaking views within this natural park nearby, perfect for outdoor enthusiasts staying in the area.
- Chester Antiques Market: Discover unique vintage treasures and collectibles in this popular market that offers a nostalgic shopping experience just moments from your rental.
- The Museum at the Historic Chester Railroad Station: Immerse yourself in local history through engaging exhibits housed in a beautifully preserved historic transportation hub.
- Farmers’ Markets and Local Food Tours: Savor fresh, regional produce and culinary delights while exploring the authentic tastes of this destination’s vibrant food scene.
Other Places to Stay in Chester, NY
Goosepond Mountain State Park
Sugar Loaf
The Rock Sports Complex
Castle Fun Center
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Explore local outdoor adventures and cultural sites to maximize your time in this scenic region, making your stay more enriching and memorable.
- Choose the Right Accommodation: Select a well-located vacation rental that offers easy access to the area's attractions and natural beauty for a truly convenient experience.
- Experience Local Cuisine: Take advantage of nearby dining options or prepare meals in your rental to enjoy authentic flavors unique to here’s culinary scene.
- Engage with the Community: Participate in local events or visit community spots to gain a deeper understanding of this destination’s unique culture and charm.
Transportation Options
- Chester Bus Station: This local hub offers convenient bus services to and from nearby cities, making it easy to explore the surrounding region without a car.
- Private Car Rentals: Many visitors opt for rental cars in Chester, providing flexible transportation to enjoy the area's scenic attractions and outdoor activities.
- Taxi and Ride-Sharing Services: On-demand taxis and ride-sharing options are readily available here, offering quick and reliable transportation around the town and its outskirts.
- Airport Shuttles: Several shuttle services operate between the regional airports and this destination, ensuring a smooth arrival and departure experience for your trip.
Local Customs Options
- Chester County Fair: You can experience the local community spirit by attending the county fair, a cherished tradition that showcases regional crafts, food, and entertainment.
- Farmers' Markets: Visiting the farmers' markets offers a chance to enjoy fresh, locally-grown produce and support regional farmers in this area.
- Historical Preservation: Respect for historical sites is integral here, with many preservation efforts reflecting the area's appreciation for its heritage and traditions.
- Community Events: Participating in seasonal festivals and outdoor gatherings allows you to immerse yourself in the region's friendly and welcoming culture.
Chester Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Chester?
There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester:
- Country House w/Hot Tub, Deck, Grill & Fire Pit
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
- Spectacular Historic Mansion w/Pool&Tennis
- Cozy studio on 36 acres close to everything in Warwick
- Incredible Ranch in the Woods - Peace and Luxury!
- Cozy cottage, beautiful views, close to Warwick!
- Summerville Getaway (30 min to Mt. Creek)
- Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY
- Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
2. How many vacation rentals have private pools in Chester?
There are 6 vacation rentals with private pools near Chester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
4. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 66 in the Chester 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 Chester.
5. What is the cancellation policy for vacation rentals in Chester, New York?
Cancellation policies vary by property, so it’s important to review the specific listing details before booking. You can find this information in the rental's policy section or contact the property owner directly for clarification.
6. Are there any specific house rules I should be aware of when booking a rental here?
Each property may have its own set of house rules related to check-in/check-out times, pet policies, and occupancy limits. Be sure to read these details in the listing description or reach out to the host for any clarifications.
7. How do I verify the safety and cleanliness standards of vacation rentals in this area?
Safety and cleanliness standards are typically outlined in the listing details. You may also contact the property owner to inquire about cleaning protocols and safety measures implemented for your peace of mind.
8. What amenities are usually included in vacation rentals around the region?
Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and parking. For specific amenities, always review the detailed listing or contact the owner directly to ensure your needs are met during your stay.
9. Is there a minimum night stay requirement for booking here?
Minimum stay requirements depend on the individual rental. Check the specific listing for details or contact the host directly to confirm availability and stay duration policies.
Chester Top Rated Vacation Rentals
Hotel
8.2(516 Reviews)
6 Baths
301.39 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $295/Night
7 Nights - US $2,062
House
10.0(1 Review)
5 Bedrooms
4 Baths
13 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $480/Night
7 Nights - US $3,360
House
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $473/Night
7 Nights - US $3,311
House
7.0(17 Reviews)
6 Bedrooms
3 Baths
16 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $886/Night
7 Nights - US $6,204
Villa
6.6(4 Reviews)
9 Bedrooms
4 Baths
25 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,410/Night
7 Nights - US $9,868
Villa
5.0(1 Review)
7 Bedrooms
5 Baths
14 Guests
4600 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $655/Night
7 Nights - US $4,585
Other
4.8(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Pool
- View
- Kitchen
US $350/Night
7 Nights - US $2,450
House
4.0(1 Review)
5 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $591/Night
7 Nights - US $4,137
