Best Vacation Homes in Chester
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R4,045/Night
For 7 Nights R28,310
247.57 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Ski Chalet
- Pet Friendly
- Parking
- Internet
R2,407/Night
For 7 Nights R16,845
R2,279/Night
For 7 Nights R15,946
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,062/Night
For 7 Nights R35,425
1194.79 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R3,696/Night
For 7 Nights R25,873
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,820/Night
For 7 Nights R33,740
754 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Oceanfront
- Hot Tub
- Fireplace/Heating
R4,733/Night
For 7 Nights R33,135
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,294/Night
For 7 Nights R30,060
Chester Luxury Rentals
3767 ft²
10 Guests
1 Bedroom
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R15,035/Night
For 7 Nights R105,243
4792 ft²
8 Guests
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R12,710/Night
For 7 Nights R88,970
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R12,317/Night
For 7 Nights R86,223
4 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R12,176/Night
For 7 Nights R85,241
6 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Parking
- Air Conditioner
- Internet
R11,980/Night
For 7 Nights R83,851
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R11,441/Night
For 7 Nights R80,090
10 Guests
5 Bedrooms
4 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
R11,268/Night
For 7 Nights R78,879
14 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
R10,659/Night
For 7 Nights R74,611
Chester Pet Friendly Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R1,695/Night
For 7 Nights R11,857
247.57 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Ski Chalet
- Hot Tub
- Fireplace/Heating
- Pet Friendly
R2,854/Night
For 7 Nights R19,969
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Pet Friendly
- Kitchen
R1,628/Night
For 7 Nights R11,399
2766 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Ski Chalet
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R2,514/Night
For 7 Nights R17,598
301.39 ft²
12 Guests
3 Bathrooms
Family Friendly
Resort
- Private Pool
- Hot Tub
- Fireplace/Heating
R2,678/Night
For 7 Nights R18,743
800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,930/Night
For 7 Nights R27,509
R3,423/Night
For 7 Nights R23,960
982 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R2,709/Night
For 7 Nights R18,955
Chester Large Vacation Homes
2998 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R5,796/Night
For 7 Nights R40,576
398.26 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
House
- Balcony/Terrace
- View
- Parking
R4,749/Night
For 7 Nights R33,233
3000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
R6,093/Night
For 7 Nights R42,653
R9,554/Night
For 7 Nights R66,875
1 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
R9,261/Night
For 7 Nights R64,831
200 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
R4,049/Night
For 7 Nights R28,343
2691 ft²
14 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R7,660/Night
For 7 Nights R53,628
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
R3,330/Night
For 7 Nights R23,306
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 right time to visit here can greatly enhance your experience, as the region offers different charms throughout the year, making it essential to plan your stay during the season that best aligns with your vacation goals in Chester, Nova Scotia, Canada.
Peak Season Highlights
June to September
During the summer months, you can enjoy warm weather and longer daylight hours that make exploring the region's scenic beauty more delightful.
Average Temperature Daytime: 20°C to 25°C - Nighttime: 12°C to 16°C
December to February
Winter offers a charming experience with snowfall and festive celebrations, attracting visitors seeking a cozy escape in this popular destination.
Average Temperature Daytime: -1°C to 3°C - Nighttime: -5°C to -1°C
Off-Season Highlights
April to May
Springtime brings milder weather and blooming landscapes, making it an ideal time to enjoy peaceful stays before the busy summer season begins.
Average Temperature Daytime: 8°C to 15°C - Nighttime: 3°C to 8°C
October to November
Autumn features vibrant foliage and cool temperatures, giving you a serene environment for exploring the area's natural beauty away from peak crowds.
Average Temperature Daytime: 10°C to 15°C - Nighttime: 4°C to 8°C
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 grilling facilities to prepare meals while soaking in the scenic views of the region.
- Benefit from private patios or decks ideal for relaxing and appreciating the fresh air of this destination.
- Take advantage of spacious yards perfect for outdoor games and family activities in the area.
- Make use of on-site fire pits to gather around and share stories under the stars.
- Access waterfront areas or nearby beaches for swimming, kayaking, or simply unwinding by the water.
- Utilize outdoor dining spaces that allow you to savor meals with picturesque surroundings.
- Explore nearby walking or biking trails that provide an active way to enjoy the natural beauty here.
Top Attractions Around Chester
What attractions are nearby?
In this charming area, you can explore scenic outdoor activities, enjoy local dining experiences, and take part in water-based adventures just moments from your vacation rental.
Family Activities
- Chester Waterfront Park: Enjoy a relaxing day at this scenic park with family-friendly walking trails and beautiful views of the harbor.
- Chester Playhouse: Experience local culture with family-friendly performances and entertainment suitable for all ages at this charming theater.
- Chester Golf Club: Spend quality time together on the lush fairways, perfect for both beginners and experienced golfers seeking fun in the area.
- Chester Yacht Basin: Explore the marina's waterfront environment, offering opportunities for family boat watching or renting a vessel to discover the region’s waters.
Adult Activities
- Exploring the Chester Golf Course: You can enjoy a round of golf on this scenic course, renowned for its stunning views and challenging layout.
- Enjoying local craft beverages at nearby breweries: Sample regional brews at some of the area's popular breweries, perfect for a relaxing adult outing.
- Participating in sailing or boat tours: Experience the region's maritime charm by taking a guided sailing trip or boat tour along the coast.
- Visiting art galleries and cultural centers: Discover vibrant local artistry and cultural expressions within the area’s charming galleries and studios.
Other Places to Stay in Chester, NS
East River Point
Aldersville
Northwest Cove
Southwest Cove
New Ross
Fox Point
Upper Blandford
Middle River
Bayswater
Mill Cove
Western Shore
Chester
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take advantage of the region's renowned seafood and seaside eateries to savor authentic flavors during your stay.
- Embrace Water Activities: Enjoy the calm waters with kayaking or sailing, experiencing the area's scenic coastline firsthand.
- Visit Nearby Attractions: Plan day trips to explore local landmarks and natural beauty that showcase the region’s charm.
- Book in Advance: Secure your preferred vacation rentals early to ensure a seamless and stress-free experience in this sought-after destination.
Transportation Options
- Chester Harbour Ferry Service: Offers scenic and convenient transportation across the harbor, making it easy to explore the area from your vacation rental.
- Nova Scotia Transit Bus: Provides public transit options connecting Chester to surrounding communities and key destinations within the region.
- Private Taxi and Ride-Sharing Services: Available for flexible travel around the destination, allowing you to reach local attractions comfortably from your accommodation.
- Car Rentals: A practical choice if you prefer exploring at your own pace, with several rental agencies serving travelers in and around Chester.
Local Customs Options
- Welcoming Community Spirit: The area's residents pride themselves on their friendly hospitality, making visitors feel at home from the moment they arrive.
- Maritime Seafood Traditions: Here, you’ll find locals cherish their fishing heritage, evident in the fresh seafood served during community festivals and gatherings.
- Respect for Nature and Environment: Preserving the natural beauty of this coastal destination is a key local custom, encouraging eco-friendly practices among visitors and residents alike.
Frequently Asked Questions About Chester?
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:
- Spectacular Oceanfront Living in Authentic Fishing Village
- Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
- Adventure Awaits at Salt & Tide Ocean Retreat
- The Nest at Deep Cove
- Superb Oceanfront with Optional Boathouse
- Cooperage Cottage - Peaceful & Family Friendly, Oceanfront
- Ahoy!.Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions
- Stunning Ocean Front cottage, minutes from the beach
- Cozy Oceanfront Escape with Hot Tub
- Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove
2. How many vacation rentals have private pools in Chester?
There are 1 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 170 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, Nova Scotia?
Cancellation policies vary by property. To understand the specific terms, please review the listing details or contact the property owner directly for the vacation rental you're interested in.
6. How do I make a secure reservation at a Chester vacation rental?
Reservations are made through a secure booking system that ensures your personal and payment information is protected. For any questions about the booking process, reach out to the host or support team.
7. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning charges, service fees, or taxes may apply depending on the property. Details are provided during the booking process or in the listing description.
8. Can I modify or cancel my reservation if my plans change?
Modification and cancellation policies depend on the individual property. Please review the property's policies before confirming your booking or contact the host for assistance.
9. What amenities can I expect in vacation rentals in this destination?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and laundry services. Check the specific listing for a comprehensive list of available amenities.
Chester Top Rated Vacation Rentals
2700 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R5,147/Night
For 7 Nights R36,030
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
R10,411/Night
For 7 Nights R72,877
2585 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R8,130/Night
For 7 Nights R56,915
780 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Spa
- Fireplace/Heating
R1,793/Night
For 7 Nights R12,561
2700 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Spa
- Fireplace/Heating
- Pool
R9,637/Night
For 7 Nights R67,464
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
R6,839/Night
For 7 Nights R47,871
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R5,109/Night
For 7 Nights R35,768
850 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
R3,243/Night
For 7 Nights R22,701
