Best Vacation Homes in Chester
House
10.0(64 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
Parking
Kitchen
Internet
Pet Friendly
US $258/Night
7 Nights - US $1,809
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1194.79 ft²
Oceanfront
EV Charge Station- Parking
Ocean View
US $226/Night
7 Nights - US $1,582
US $179/Night
7 Nights - US $1,255
Cottage
10.0(31 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
Balcony/Terrace
View
US $270/Night
7 Nights - US $1,891
Ski Chalet
10.0(1 Review)
2 Bedrooms
1 Bath
2 Guests
269.1 ft²
Hot Tub- Parking
- Balcony/Terrace
Air Conditioner
US $176/Night
7 Nights - US $1,234
Cottage
10.0(26 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $315/Night
7 Nights - US $2,205
Cottage
10.0(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $128/Night
7 Nights - US $898
Ski Chalet
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
2766 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,303
Chester Luxury Rentals
House
10.0(7 Reviews)
5 Bedrooms
4 Baths
12 Guests
3900 ft²
- Oceanfront
- Hot Tub
- Parking
Spa
US $943/Night
7 Nights - US $6,602
House
10.0(2 Reviews)
4 Bedrooms
6 Baths
8 Guests
4792 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $880/Night
7 Nights - US $6,159
New
House
4 Bedrooms
3 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $862/Night
7 Nights - US $6,037
House
5 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $861/Night
7 Nights - US $6,030
House
2 Bedrooms
3 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $852/Night
7 Nights - US $5,967
House
10.0(1 Review)
6 Bedrooms
4 Baths
14 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $796/Night
7 Nights - US $5,573
Cottage
10.0(1 Review)
4 Bedrooms
1 Bath
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $762/Night
7 Nights - US $5,336
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Parking
Pool- Kitchen
- Air Conditioner
US $708/Night
7 Nights - US $4,958
Chester Pet Friendly Vacation Rentals
House
10.0(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $356/Night
7 Nights - US $2,489
Ski Chalet
9.9(20 Reviews)
1 Bedroom
1 Bath
2 Guests
247.57 ft²
- Parking
- Internet
- Pet Friendly
Child Friendly
US $147/Night
7 Nights - US $1,030
Cottage
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Internet
- Pet Friendly
US $100/Night
7 Nights - US $697
Apartment
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $182/Night
7 Nights - US $1,271
Ski Chalet
9.6(29 Reviews)
1 Bedroom
1 Bath
2 Guests
247.57 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
US $174/Night
7 Nights - US $1,221
House
10.0(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
1600 ft²
- Oceanfront
- Hot Tub
- Parking
- Spa
US $331/Night
7 Nights - US $2,314
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $384/Night
7 Nights - US $2,686
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
648 ft²
- Parking
- Kitchen
- Internet
- Pet Friendly
US $366/Night
7 Nights - US $2,565
Chester Large Vacation Homes
Cottage
8.6(55 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $216/Night
7 Nights - US $1,515
House
9.5(40 Reviews)
5 Bedrooms
3 Baths
12 Guests
398.26 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $290/Night
7 Nights - US $2,032
Villa
1 Bedroom
5 Baths
10 Guests
3767 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $692/Night
7 Nights - US $4,843
House
10.0(22 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $754/Night
7 Nights - US $5,279
House
10.0(5 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Oceanfront
- Hot Tub
- Parking
- Spa
US $678/Night
7 Nights - US $4,749
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
1 ft²
- Child Friendly
US $554/Night
7 Nights - US $3,880
House
9.8(19 Reviews)
5 Bedrooms
5 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $561/Night
7 Nights - US $3,930
House
9.6(12 Reviews)
6 Bedrooms
2 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $320/Night
7 Nights - US $2,240
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.
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
Upper Blandford
Fox Point
Middle River
Chester
Mill Cove
Chester Basin
Western Shore
Bayswater
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.
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:
- Adventure Awaits at Salt & Tide Ocean Retreat
- The Nest at Deep Cove
- Stunning Ocean Front cottage, minutes from the beach
- Coffee With A View Of Deep Cove
- Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.
- Oceanfront cozy comfortable cottage!
- Charming coastal beach house, with beautiful ocean views
- Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
- Cozy tranquil cottage, ocean view, nestled on the edge of a forest
- The Lower Deck Ocean Escape/Paddle Boards, Kayaks and Bikes
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 169 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
Condo
9.6(9 Reviews)
2 Bedrooms
2 Baths
5 Guests
2700 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $274/Night
7 Nights - US $1,915
Resort
9.0(9 Reviews)
3 Baths
16 Guests
301.39 ft²
Private Pool- Hot Tub
- Parking
- Pool
US $164/Night
7 Nights - US $1,146
Cottage
10.0(67 Reviews)
1 Bedroom
1 Bath
3 Guests
780 ft²
- Oceanfront
Breakfast- Parking
- Pool
US $110/Night
7 Nights - US $768
House
10.0(32 Reviews)
5 Bedrooms
2 Baths
10 Guests
2700 ft²
- Breakfast
- Parking
- Pool
- Spa
US $589/Night
7 Nights - US $4,125
House
10.0(21 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $418/Night
7 Nights - US $2,927
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $312/Night
7 Nights - US $2,187
House
9.6(21 Reviews)
4 Bedrooms
3 Baths
8 Guests
2585 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $563/Night
7 Nights - US $3,944
Cottage
9.6(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $198/Night
7 Nights - US $1,388
