We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Chester

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    S$226 Average
    |||
    |||
    S$0S$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Chester area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Chester
    Sort by:
    Default
    5 bedroom quiet and spacious retreat1 / 27
    (2)Excellent
    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Serenity1 / 16
    (9)Excellent
    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Breath taking Ocean Harbour Front 3 Bedroom 2 Bath1 / 34
    (3)Very good
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: In one of the historic homes of Lunenburg, a door gives way to a surprising find. Upstairs is an inviting, creatively designed and spacious loft style 1 bedroom 1 bath accommodation, that is upbeat with unique flourish, original art and maximum comforts. Through a private...
    View all property information
    Location Information
    Chester, Southwest Nova Scotia B0J 1K0
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: Take in as much beauty as the undeveloped Nova Scotia waterfront has to offer, from this charming, private 2-story home. Located at the end of a winding private drive, this cape-style shingled cottage is sequestered in a pristine and natural setting of 3.75 acres with 300-ft of...
    View all property information
    Location Information
    Chester, Southwest Nova Scotia B0J 1K0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Washer
    • Parking
    • Wi-Fi
    • Private Garden
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three storey historical home features traditional character and charm. Located in the historic seaside village of Chester. The House sleeps 10 people - 3 queen beds, and 2 single beds and a set of single bunk beds which are in the connecting room off one of the queen bedrooms. Lots of outdoor...
    View all property information
    Location Information
    Chester, Southwest Nova Scotia B0J 1J0
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    #30 Captains Watch Oceanfront Retreat, McGraths Cove  NS1 / 16
    (3)Very good
    Chester
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2017
    Our group of 8 retirees stayed in this amazing home from Sept 9 -23 2017. We enjoyed this well equiped waterfront property and used it as a base for touring around Nova Scotia...
    Reviewed 3 June 2017
    This very nice home on a great place in a nice and friendly comunity needs cleaning up inside. Dishes, kitchenware, pots and pans was dirty and bevore using we have to clean up...
    See all reviews
    About this property
    RENTAL DESCRIPTION: The locals say that Nova Scotia is the place where heaven meets earth, and nowhere is that more true than on this Peggy's Cove area oceanfront retreat. To see this 5 Bedroom 3.5 bath newly restored home and its picture-perfect sheltered cove, is to fall in love. It is a great...
    View all property information
    Location Information
    Chester, Southwest Nova Scotia B0J 1K0
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Chester
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 200-year-old carriage house is Chester’s hidden gem. Completely renovated by a renowned East Coast architect, this property is the perfect place to relax and get away. It is located in the heart of the Chester village, within walking distance from restaurants, Nova Scotia`s oldest pub The...
    View all property information
    Location Information
    Chester, Southwest Nova Scotia B0J1J0
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
    Make Enquiry
    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: This delightful single level bungalow cottage is nestled on Nova Scotia's amazing South Shore area of Green Bay. Here, you are directly across from a pristine white sand beach and close to Risser's Beach Provincial Park. Wake up to the sounds of the ocean and surf while enjoying...
    View all property information
    Location Information
    Chester, Southwest Nova Scotia B0J 1K0
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    The following rentals are within 15 kilometres of Chester.
    Cherry Lane Cottage Mahone Bay NS1 / 12
    (4)Excellent
    Mahone Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Grill
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2017
    Cherry Lane cottage was clean and in a fantastic location. The cottage was well stocked with towels, linens, and cooking utensils. The beds were comfortable. There was also a...
    Reviewed 21 September 2016
    Jim and I have traveled extensively over the years, but seldom have we enjoyed our accommodation as much as Cherry Lane Cottage. It is charming, comfortable, well equipped and a...
    See all reviews
    About this property
    Cozy 2 storey cottage on a narrow, quiet lane in the heart of pictureque, tranquil Mahone Bay, Nova Scotia. Within walking distance to downtown, the waterfront, restaurants, bistros, coffee shops, pub, shopping, waterfront festivals and events. Fully equipped kitchen, private deck with BBQ, bed...
    View all property information
    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Save time - get the best Chester rentals sent straight to your email!
    Get the List
    Western Shore
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is situated on a peninsula and boasts ocean views from every window. Located on a quiet cove you can enjoy your own small beach area and clear views of the famous Oak Island. In the summer months the cove fills with sailboats and kayakers. Wake up in the morning to an ocean view at the...
    View all property information
    Location Information
    Western Shore, Southwest Nova Scotia B0J 1J0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Far Far Away Guesthouse1 / 22
    (5)Excellent
    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2016
    This house was a very cozy and comfortable base for our travels around Mahone Bay. When we first arrived we found it it was farther from Mahone Bay than we had anticipated, but...
    Reviewed 14 August 2016
    The Far Far Away Guesthouse was exactly what my family of three needed. It was far enough away from the hustle & bustle of the city, and a close drive to attractions. My 5...
    See all reviews
    About this property
    Far Far Away is a Canada Select 4 Star guesthouse located directly between Chester and Mahone Bay; a ten minute drive in either direction and 25 minutes to the UNESCO World Heritage Town of Lunenburg. The guest house shares a driveway with an early 1900s home and has oodles of privacy in the...
    View all property information
    Location Information
    Mahone Bay, Southwest Nova Scotia B3J 2Y3
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    #4 Heisler House Haven, Mahone Bay  NS1 / 14
    (1)Excellent
    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    We were bumped from our original booking in Lunenburg to this amazing apartment on the bay. The deck alone is reason enough to stay here. Even though it is on the main road...
    See all reviews
    About this property
    RENTAL DESCRIPTION: MAHONE BAY 2BR TOWNHOUSE IN TOWN NEAR ART GALLERIES, DINING, & SHOPS. The views from this second-level townhouse, located in the heart of Mahone Bay, are one of the most photographed scenes in Nova Scotia. From your waterside balcony, you look out onto the Mahone Bay Harbor and...
    View all property information
    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    #34 Emily's Seaside Escape, Hubbards1 / 17
    (1)Very good
    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    We enjoyed our stay here, it was very quiet. Great wifi, decent location and clean cottage. 10 minute drive to Hubbard's, where you can find grocery, liquor and restaurants...
    See all reviews
    About this property
    RENTAL DESCRIPTION: Relax and surround yourself with the calming ocean views of Emily's Seaside Escape. Early riser's can savour their morning beverage on the spacious deck awakening to the glorious sunrise over St. Margaret's Bay. Watch as the sailboats and fishing vessels venture off to seize the...
    View all property information
    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Over The Way Cottage1 / 17
    (1)Very good
    Western Shore
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    The owner Jay did an outstanding job of ensuring the unit was well stocked with everything. This included local organic coffee and local wine. There was really nothing that was...
    See all reviews
    About this property
    Over The Way Cottage offers pet-friendly accommodations in Martin's Point, Nova Scotia. It's conveniently located between Mahone Bay and Chester. Close to local attractions but out of the way enough to feel like a rural retreat. Originally built in the early 1900s, by the owners great grandparents,...
    View all property information
    Location Information
    Western Shore, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Blandford
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to a fully renovated four bedroom three bathroom two story Cape Cod home on the cove. Enjoy the views of the ocean from within this newly appointed retreat. Watch the sailboats and fishing boats while you soak up the sun either on the flat pebble beach out front or hanging out on the large...
    View all property information
    Location Information
    Blandford, Southwest Nova Scotia B0J 1T0
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    List your property
    Owner log in