Discover your perfect Chester Vacation Rentals.
Discover Your Perfect Chester Vacation Homes
Best Vacation Homes in Chester
10.0
(42 Reviews)
- Air Conditioner
- Parking
- TV
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House
9.0
(3 Reviews)
- Air Conditioner
- Parking
- View
10.0
(18 Reviews)
- Air Conditioner
- Pet Friendly
- TV
10.0
(12 Reviews)
- Parking
- TV
- Security/Safety
10.0
(2 Reviews)
- Air Conditioner
- Security/Safety
- Bedding/Linens
9.8
(11 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.8
(6 Reviews)
- Air Conditioner
- Pet Friendly
- TV
9.6
(31 Reviews)
- Air Conditioner
- Parking
- TV
Chester Luxury Rentals
New
- Parking
- Pool
- TV
New
- Air Conditioner
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- TV
New
- Air Conditioner
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- TV
10.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
9.6
(14 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
New
- Air Conditioner
- Parking
- Pool
9.8
(20 Reviews)
- Air Conditioner
- Parking
- Pool
New
- Security/Safety
- Bedding/Linens
- Wellness Facilities
Chester Pet Friendly Vacation Rentals
9.4
(6 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
New
- Air Conditioner
- Parking
- Pet Friendly
New
- Air Conditioner
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- Pet Friendly
10.0
(24 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.6
(26 Reviews)
- Parking
- Pet Friendly
- Pool
9.6
(15 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.6
(12 Reviews)
- Parking
- Pet Friendly
- TV
Chester Large Vacation Homes
10.0
(32 Reviews)
- Air Conditioner
- Parking
- Pool
New
- Air Conditioner
- Balcony/Terrace
- Bedding/Linens
New
- Air Conditioner
- Pet Friendly
- Bedding/Linens
New
- Air Conditioner
- Wheelchair Accessible
- Kitchen
New
- Parking
- Pet Friendly
- TV
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.
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
Other Places to Stay in Chester, NS
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:
- Serenity Tiny House Cottage in Chester
- Cooperage Cottage - Peaceful & Family Friendly, Oceanfront
- Ahoy!.Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions
- Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove
- The Captain’s Quarters 2 bedroom harbourview condo
- Seascape,Art Deco cottage
- Seapearl Studio: Cozy Coastal Retreat in the Heart of Chester
- White Cottage, An East Coast Architectural Masterpiece
- Gorgeous Oceanfront Estate with Heated Pool
- A Sailor's Paradise - Stevens Cove Guest Quarters
2. 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:
3. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 61 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.
Chester Top Rated Vacation Rentals
10.0
(67 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(21 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(2 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.6
(5 Reviews)
- Air Conditioner
- Pool
- View
8.6
(4 Reviews)
- Parking
- Pet Friendly
- Pool
New
- Air Conditioner
- Parking
- Pool