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Chester Vacation Rentals

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    Travelers to Chester are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 40 Rentals in Chester
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    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Serenity1 / 16
    (5)Excellent
    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We were a family of 5 with 3 children and the house was just perfect. The kitchen is fully equipped. If you like cooking at home you will not be disappointed, Sandra has all you...
    Reviewed August 17, 2016
    The house is beautiful- even better than in the pictures. Sandy and Bill exceptionally welcoming- even took us on a trip around the harbour in their boat. Chester is a wonderful...
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    About this property
    Come to beautiful Chester and Stay in this Storybook 1600 Sq ft Cottage. It sits on a meticulously landscaped 2 acres overlooking the Coveside Stable. This cottage has all of the ammenities of home and is less than 5 minutes to the village of Chester, well known to sailors all over the world. The...
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    Chester, Southwest Nova Scotia B0J 1J0
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Chester
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    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...
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Breath taking Ocean Harbour Front 3 Bedroom 2 Bath1 / 34
    (1)Excellent
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
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    Reviewed April 26, 2017
    This home is a real find right on the water in the heart of Chester. You are within walking distance to restaurants, shops, the Tancook Island Ferry and the Yacht Club. We fell...
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    About this property
    Breath taking Harbour Front 3 Bedroom 2 Bath Condo. Located on historic Chester Front Harbour. Private steps to the crystal clean water perfect for swimming in the summer months .The perfect mix. Master bedroom custom on suite with rain shower, walk in closet Recently renovated and excellent mix...
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    Chester, Southwest Nova Scotia B0J 1J0
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Cozy 1 bedroom cottage with a loft in the heart of Chester. Newly renovated. Full kitchen, living room and bathroom. Beautiful gardens surrounding the property. Cable and Wireless Internet Provided. Not far from Chester's beautiful waterfront. In walking distance there is the Yacht Club, Captain's...
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    Chester, Southwest Nova Scotia B0J 1J0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    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...
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    Chester, Southwest Nova Scotia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    #30 Captains Watch Oceanfront Retreat, McGraths Cove  NS1 / 16
    (2)Very good
    Chester
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
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    Reviewed June 3, 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...
    Reviewed October 14, 2016
    I've stayed in many VRBO properties over the year. This is the BEST equipped property in which I've ever stayed. It was well-stocked with condiments from previous guests...
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    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...
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    Chester, Southwest Nova Scotia
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
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    RENTAL DESCRIPTION: PRIVATE 2 BEDROOM COTTAGE NEAR HISTORIC LUNENBURG, MAHONE BAY & STONEHURST. A magical private cottage built on the rocks of Schooner Cove where eagles, osprey and seabirds fly by at eye level. Panoramic views from every window and the deck offers wonderful sunrises and sunsets....
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    Chester, Southwest Nova Scotia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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...
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    Chester, Southwest Nova Scotia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    RENTAL DESCRIPTION: DELIGHTFUL WATERFRONT 2BR/2BA HOME IN CHESTER'S BACK HARBOUR W/DOCK. Chester Waterfront with Private Dock, 4-Star. Extraordinary Location. This delightful waterfront home, nestled on a private lane, has a fabulous view of Chester's sheltered Back Harbour. Surrounded by peaceful...
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    Chester, Southwest Nova Scotia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Satellite TV
    • Patio
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    • Central Heating
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    Pet friendly
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    Smoking allowed
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    Chester, Southwest Nova Scotia B0J 1J0
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Satellite TV
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
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    • Washer
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Central Heating
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    Pet friendly
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    Smoking allowed
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    Chester, Southwest Nova Scotia B0J 1K0
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
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    Chester, Southwest Nova Scotia B0J1T0
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Chester, Southwest Nova Scotia B0J 1K0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chester
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
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    Chester, Southwest Nova Scotia B0J 1J0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Central Heating
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    Chester, Southwest Nova Scotia B0J 1J0
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Chester, Southwest Nova Scotia B0J 1J0
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chester
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Chester, Southwest Nova Scotia B0J1J0
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    The following rentals are within 10 miles of Chester.
    Loon Lodge on Mahone Bay Harbor with Famous Waterfront View! Boats and Bikes!1 / 20
    (1)Very good
    Mahone Bay
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Central Heating
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    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2016
    The hosts tried in every way to anticipate the needs of guests. I would have given 5 stars but we, unfortunately, chose a week during an extended drought and the water comes...
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    About this property
    NOTE: LOON LODGE ON MAHONE BAY HARBOR HAS BEEN COMPLETELY BOOKED OF 2017 FOR SOME TIME. BOOK EARLY FOR 2018 AT OUR NEW MONTHLY RATES AND SAVE ON ONE OF THE FINEST WATERFRONT VIEWS IN EASTERN NORTH AMERICA! The 3 Historic Churches on Mahone Bay Harbor are one of Canada's most famous views, and...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Heritage Cape on Main Street Mahone Bay1 / 15
    (2)Excellent
    Mahone Bay
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Central Heating
    • Wi-Fi
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    • Private Yard
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    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2015
    We stayed for a couple of nights and wish we could have stayed longer. The house is beautifully decorated, quaint and cosy. The bathroom and bedrooms were impeccable, the...
    Reviewed June 12, 2015
    Extremely cozy place. Beautifully decorated. Well equipted with essential kitchen tools. Top quality bed & bath linens. Very comfortable beds in both rooms. Lovely deck area...
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    About this property
    Conveniently located on Main Street, Mahone Bay, this updated Cape-style home offers the privacy of a country getaway within a short walk from downtown Mahone Bay. Two bedroom, one bath, full kitchen, spacious living room, dining room and laundry facilities. The backyard contains a large lawn area...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Balcony
    • Central Heating
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located on Main Street, Mahone Bay, this cozy cottage offers the privacy of a country getaway within a short walk from downtown Mahone Bay.<BR><BR>One bedroom, one bath, includes a kitchenette, spacious living area and large private deck. Equipped with microwave, double-burner cooktop,...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cherry Lane Cottage Mahone Bay NS1 / 14
    (4)Excellent
    Mahone Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Grill
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    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 September 21, 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...
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    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...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Far Far Away Guesthouse1 / 13
    (4)Excellent
    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
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    • Satellite TV
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 2, 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 August 14, 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...
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    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...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B3J 2Y3
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Mahone Bay
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    RENTAL DESCRIPTION: COZY SEASIDE RETREAT ON MAHONE BAY SLEEPS 6 W/PRIVATE DOCK & ROW BOAT. Silver Tides is a cozy and compact seaside retreat offering easy access to the sought after sailing waters of Mahone Bay. Special features include more than a 100- ft. of ocean frontage with rock-stone...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    Reviewed 4 days ago
    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...
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    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...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    #42 Kingfisher Cottage, Mahone Bay  NS1 / 14
    (1)Excellent
    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2015
    This was our second time staying in this cottage. We stayed for 6 nights and wish we could have stayed longer. Very well equipped for cooking. Very quiet and peaceful...
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    RENTAL DESCRIPTION: UPDATED OCEANFRONT 2BR/1BA COTTAGE ON 35-ACRES W/POOL IN MAHONE BAY. Simply delightful, these three (3) refurbished oceanfront cottages on 35-acres with private swimming pool will steal your heart. Beautifully upgraded, each cottages features one floor living with a bright open...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Waterfront
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: DELIGHTFUL 2BR/1BA OCEANFRONT COTTAGE, UPGRADED W/POOL & PRIVATE DECK. Simply delightful, these three (3) refurbished oceanfront cottages on 35-acres with private swimming pool will steal your heart. Beautifully upgraded, each cottages features one floor living with a bright...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Internet Access
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: UPDATED OCEANFRONT 2BR/1 BA COTTAGE ON 35-ACRES W/POOL IN MAHONE BAY. Simply delightful, these three (3) refurbished oceanfront cottages on 35-acres with private swimming pool, will steal your heart. Beautifully upgraded, each cottages features one floor living with a bright...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    #19 Saracenia Cottage, Upper Blandford  NS1 / 18
    (3)Very good
    Blandford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: WATERFRONT 4BR/2BA CAPE HOME W/BOLD OCEAN VIEWS NEAR HISTORIC TOWNS. Saracenia Cottage is enjoying a second lease on life. This fabulous classic waterfront cape on a private paved road, has been loving restored with every modern amenity to make your stay here special. Located in...
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    Location Information
    Blandford, Southwest Nova Scotia
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    The New-Found Guest House1 / 26
    (19)Excellent
    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Satellite TV
    • Grill
    • Shared Yard
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2015
    My wife and I stayed at this cottage recently for two nights. We booked this property on the basis of the TA reviews although I didn't notice until after that, the most recent...
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    About this property
    The New-Found Guest House is located approximately 45 minutes from Halifax - Nova Scotia's capital, 5 minutes from scenic Mahone Bay and 10 minutes from historic Lunenburg - home of the Bluenose. This completely renovated loft suite is a fully-equipped, self-contained unit. It has two double beds,...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Over The Way Cottage1 / 17
    (1)Very good
    Western Shore
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    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...
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    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,...
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    Location Information
    Western Shore, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Westaway House1 / 11
    (1)Excellent
    Chester Basin
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This was the perfect place for my husband and I to spend a week exploring the Chester Basin area. The kitchen had just what we needed to cook breakfast before heading out for...
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    About this property
    The spacious flat is private and has a great outdoor space too. It shares the grounds with Westaway House Bed and Breakfast although it's in a separate building. There are views to the water from every room. The flat has a large queen bedroom, modern spa-like bathroom and combined fully outfitted...
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    Location Information
    Chester Basin, Southwest Nova Scotia B0J1K0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chester Flight and Weather Info
    Airports nearby (1)
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    YHZ
    Halifax Stanfield Intl Airport
    42.4 miles from Chester
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    Additional Chester Info

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    • Local time: 02:13 AM (ADT)
    • Exchange rate: 1 Canadian Dollars = 0.80 U.S. Dollars
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