Best Vacation Homes in Chester
Cottage
10.0(118 Reviews)
2 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $383/Night
7 Nights - US $2,680
House
10.0(2 Reviews)
8 Bedrooms
5 Baths
21 Guests
611.39 ft²
Parking
Child Friendly
Security/Safety
Guest Services
US $68/Night
7 Nights - US $473
Bed & Breakfast
9.8(16 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
Breakfast- Parking
Internet
US $233/Night
7 Nights - US $1,633
Cottage
10.0(43 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $233/Night
7 Nights - US $1,628
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
10 Guests
2852.44 ft²
Hot Tub- Balcony/Terrace
- View
Pet Friendly
US $1,548/Night
7 Nights - US $10,833
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $522/Night
7 Nights - US $3,652
Cottage
9.8(29 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $344/Night
7 Nights - US $2,409
Apartment
9.8(6 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $353/Night
7 Nights - US $2,472
Chester Luxury Rentals
House
6 Bedrooms
4 Baths
20 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $5,027/Night
7 Nights - US $35,189
House
5 Bedrooms
5 Baths
12 Guests
5000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $2,342/Night
7 Nights - US $16,397
Villa
8.0(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
Oceanfront- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,719/Night
7 Nights - US $12,031
New
House
8 Bedrooms
6 Baths
28 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,676/Night
7 Nights - US $11,734
House
3 Bedrooms
3 Baths
6 Guests
1302.43 ft²
- Hot Tub
- Fireplace/Heating
- Parking
- Internet
US $1,545/Night
7 Nights - US $10,815
House
9.8(6 Reviews)
5 Bedrooms
2 Baths
14 Guests
6000 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,499/Night
7 Nights - US $10,496
Villa
9.5(2 Reviews)
2 Bedrooms
2 Baths
10 Guests
2195.84 ft²
- Hot Tub
- Balcony/Terrace
- View
- Pet Friendly
US $1,371/Night
7 Nights - US $9,597
House
4 Bedrooms
3 Baths
10 Guests
2604.87 ft²
Private Beach- Hot Tub
- Fireplace/Heating
Pool
US $1,189/Night
7 Nights - US $8,323
Chester Pet Friendly Vacation Rentals
Apartment
8.8(15 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $346/Night
7 Nights - US $2,420
House
9.2(8 Reviews)
4 Bedrooms
2 Baths
8 Guests
2497.23 ft²
- Hot Tub
Skiing- Balcony/Terrace
- View
US $332/Night
7 Nights - US $2,325
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $442/Night
7 Nights - US $3,094
Apartment
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $145/Night
7 Nights - US $1,016
House
1.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Pet Friendly
- Parking
- Air Conditioner
US $280/Night
7 Nights - US $1,960
House
9.8(17 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $566/Night
7 Nights - US $3,963
House
9.4(13 Reviews)
2 Bedrooms
1 Bath
5 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $661/Night
7 Nights - US $4,626
House
9.2(59 Reviews)
2 Bedrooms
1 Bath
4 Guests
570 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Child Friendly
US $137/Night
7 Nights - US $961
Chester Large Vacation Homes
House
10.0(12 Reviews)
5 Bedrooms
4 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $642/Night
7 Nights - US $4,495
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
2604.87 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $858/Night
7 Nights - US $6,008
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $199/Night
7 Nights - US $1,390
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
2600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,110/Night
7 Nights - US $7,770
Bed & Breakfast
9.8(25 Reviews)
4 Bedrooms
2 Baths
10 Guests
452.08 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $180/Night
7 Nights - US $1,261
Villa
10.0(4 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $874/Night
7 Nights - US $6,121
House
5 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $624/Night
7 Nights - US $4,365
House
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $476/Night
7 Nights - US $3,331
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?
To make the most of your stay, consider visiting during the shoulder seasons when this destination offers a peaceful atmosphere and favorable weather for exploring the area’s charming surroundings.
Peak Season Highlights
May to June
During late spring to early summer, the area experiences warm weather ideal for outdoor activities and exploring local scenery.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
September to October
Early fall offers crisp air and colorful foliage, making it a popular time for enjoying scenic drives and outdoor recreation.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
January to February
Mid-winter months are quieter, with cooler temperatures perfect for those seeking a peaceful retreat in a cozy vacation rental.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
November to December
Late fall into early winter is less busy, offering a tranquil atmosphere suitable for relaxing getaways before the holiday season begins.
Average Temperature Daytime: 40-50°F - Nighttime: 30-40°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 dining areas perfect for al fresco meals amidst the scenic surroundings.
- Relax in a private backyard with lush landscaping and space for outdoor recreation.
- Take advantage of a swimming pool to cool off during the warmer months in this region.
- Make the most of a spacious patio or deck area ideal for entertaining guests.
- Explore nearby hiking trails and nature walks directly from your rental property.
- Benefit from outdoor fireplaces or fire pits, providing cozy evenings under the stars.
- Have access to well-maintained gardens or outdoor spaces that highlight the area's natural beauty.
Top Attractions Around Chester
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities and local attractions that showcase the charm of this destination’s surroundings, making your stay here both relaxing and memorable.
Family Activities
- Stroll through the Roxbury Land Trust preserves: Experience family-friendly outdoor adventures just a short drive from Chester, where you can enjoy scenic walking trails and nature exploration.
- Visit Patriots Path Conservation Area: Engage in outdoor activities such as hiking and picnicking in this beautiful area that offers a peaceful escape within reach of your vacation rental.
- Explore local farm stands and markets: Taste fresh, local produce and treats while supporting regional farmers, making it a delightful activity for families staying nearby.
- Enjoy family fun at local parks: Spend quality time at parks with playgrounds and open spaces designed for children, ideal for relaxing days in this part of New Jersey.
Adult Activities
- Historic Downtown Chester: Explore charming boutiques, cafes, and local art galleries in the area's vibrant downtown district, perfect for leisurely daytime outings.
- Patriot's Path Trail: Enjoy scenic hiking and biking along this popular trail that winds through the region, offering stunning views and outdoor adventure opportunities.
- Ridgewood Reservoir: Experience peaceful nature walks and birdwatching at this tranquil reservoir setting, ideal for relaxation amid natural beauty.
- Local Wineries and Breweries: Sample regional wines and craft beers at nearby vineyards and breweries, enhancing your taste of the area's culinary scene.
Other Places to Stay in Chester, NJ
The Streets of Chester Shopping Center
Chubb Park
Alstede Farms
Cooper Gristmill
Kay Environmental Center
Hacklebarney Farm Cider Mill
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to discover the nearby attractions that showcase the unique charm of this destination, making your stay more memorable.
- Plan Your Activities: Schedule outdoor adventures or cultural experiences in advance to maximize your time in this area’s vibrant community.
- Choose the Right Accommodation: Select a well-reviewed vacation rental that offers comfort and convenience, ensuring a relaxing retreat during your visit.
- Embrace the Local Cuisine: Savor regional flavors by visiting local eateries or preparing meals in your rental to enjoy the area's culinary delights.
Transportation Options
- Chester Train Station: Offering convenient rail access, this station connects you to major cities and makes exploring the broader region easy.
- Interstate 80: As a primary highway nearby, it provides straightforward road travel for those arriving by car or planning scenic drives through the area.
- Local Bus Services: These affordable transportation options help you navigate within Chester and reach surrounding destinations comfortably.
- Rental Car Services: Several providers in town offer reliable vehicle rentals, giving you the freedom to explore the region at your own pace.
Local Customs Options
- Local Greeting Customs: You’ll notice that friendly handshakes and warm welcomes are a customary way to greet neighbors here, reflecting the region's welcoming spirit.
- Community Events: Participating in local festivals and seasonal gatherings provides a wonderful opportunity to experience authentic regional traditions and connect with residents.
- Dining Etiquette: When enjoying meals at community restaurants or homes, expect a focus on leisurely dining and sharing conversations, embodying the area's communal values.
- Respect for Nature: Respect for the natural environment is deeply rooted here, so be mindful of local conservation practices during outdoor activities and exploring the area's scenic spots.
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:
- Lakeside Style and Luxury
- Beautiful Lakefront Home with Amazing Lake Views. Dog Friendly!
- Relaxing getaway near the largest lake in NJ
- Lakeside Home w/Lake Access, Dock & Water Views!
- Lee's House - Lakeview House w/3 bdrm & 1 bth
- Pickle Farm
- Charming 2-bedroom house on 2 dog friendly landscaped acres in lovely Chester
- Pendry Natirar
- Charming lakehouse on the water, 2 slip dock, full bar on the water
- 10 Mi to Morristown: Stylish Home Near Trails!
2. How many vacation rentals have private pools in Chester?
There are 8 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 241 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 Jersey?
Cancellation policies vary by listing; please review the specific terms on the property’s page or contact the owner directly to understand the options available for your reservation.
6. How do I find available vacation rentals in Chester, New Jersey?
Use the search filters on this site to narrow down your options based on dates, amenities, and preferences, ensuring you find the perfect accommodation here in the region.
7. Are there any additional fees I should be aware of when booking a vacation rental in Chester, New Jersey?
Additional fees such as cleaning, service charges, or taxes are typically listed during the booking process; review the detailed listing to understand all costs before confirming your reservation.
8. What amenities can I expect from vacation rentals in this area?
Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities, but it’s best to check each listing for specific features to suit your needs during your stay.
9. How can I contact the property owner if I have questions about my stay in Chester, New Jersey?
You can reach out directly through the messaging system provided on the listing page to ask any questions or clarify details before finalizing your booking.
Chester Top Rated Vacation Rentals
US $1,128/Night
7 Nights - US $7,898
US $636/Night
7 Nights - US $4,452
Hotel
9.2(414 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $143/Night
7 Nights - US $1,004
Hotel
9.0(757 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $145/Night
7 Nights - US $1,013
Hotel
9.0(273 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $187/Night
7 Nights - US $1,309
Hotel
9.0(106 Reviews)
6 Baths
523.13 ft²
Private Pool- Pool
- Breakfast
- Pet Friendly
US $436/Night
7 Nights - US $3,050
Hotel
9.0(82 Reviews)
8 Baths
542.23 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $166/Night
7 Nights - US $1,164
Hotel
8.8(1008 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $146/Night
7 Nights - US $1,019
