Chester Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

59 Houses

    20

    #14 Robins Nest, Lunenburg

    Southwest Nova Scotia / Chester

    Chester cottage

    1 2 7 nights min

    • 1 bedroom
    • sleeps 2
    • 7 nights min
    • Ask about children
    • Ask about pets

    Price per night from

    $97

    Price per night from

    $97

    (3) Very Good 

      34

      Breath taking Ocean Harbour Front 3 Bedroom 2 Bath

      Southwest Nova Scotia / Chester

      Chester condo

      3 6 7 nights min

      • 3 bedrooms
      • sleeps 6
      • 7 nights min
      • Nearest beach 1 mi
      • Child Friendly
      • Pet Friendly

      Price per night from

      $171

      Price per night from

      $171

        7

        Carriage House

        Southwest Nova Scotia / Chester

        Chester guest house

        2 4 5 nights min

        • 2 bedrooms
        • sleeps 4
        • 5 nights min
        • Pet Friendly

        Price per night from

        $214

        Price per night from

        $214

        (9) Excellent 

        Certificate of Excellence

          16

          Serenity

          Southwest Nova Scotia / Chester

          Chester cottage

          2 4 2 nights min

          • 2 bedrooms
          • sleeps 4
          • 2 nights min
          • Beach / lakeside relaxation
          • Nearest beach 3 mi
          • Child Friendly

          Certificate of Excellence

          Price per night from

          $171

          Responds fast!
          avg. 26 minutes

          Price per night from

          $171

          (3) Very Good 

            16

            #30 Captains Watch Oceanfront Retreat, McGraths Cove  NS

            Southwest Nova Scotia / Chester

            Chester cottage

            6 10 7 nights min

            • 6 bedrooms
            • sleeps 10
            • 7 nights min
            • Ask about children
            • Ask about pets

            Price per night from

            $235

            Price per night from

            $235

              19

              #18 Porters Place, Green Bay  NS

              Southwest Nova Scotia / Chester

              Chester cottage

              3 6 7 nights min

              • 3 bedrooms
              • sleeps 6
              • 7 nights min
              • Ask about children
              • Ask about pets

              Price per night from

              $112

              Price per night from

              $112

              (2) Excellent 

                27

                5 bedroom quiet and spacious retreat

                Southwest Nova Scotia / Chester

                Chester house

                5 14 min stay varies

                • 5 bedrooms
                • sleeps 14
                • min stay varies
                • Child Friendly
                • Pet Friendly
                • Private garden

                Price per night from

                $258

                Responds fast!
                avg. 27 minutes

                Price per night from

                $258

                  19

                  Historic Home in the Heart of Chester Nova Scotia

                  Southwest Nova Scotia / Chester

                  Chester house

                  5 10 3 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 3 nights min
                  • Child Friendly
                  • Pet Friendly
                  • Private garden

                  Price per night from

                  $343

                  Responds fast!
                  avg. 47 minutes

                  Price per night from

                  $343

                  Great rentals within 20 miles that match your search

                  Distance approx 13.47 km from Chester

                  (3) Very Good 

                    21

                    Secluded ocean-front country home

                    Halifax Region / Queensland

                    Queensland house

                    4 11 7 nights min

                    • 4 bedrooms
                    • sleeps 11
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Private garden

                    Price per night from

                    $256

                    Responds fast!
                    avg. 14 minutes

                    Price per night from

                    $256

                    Distance approx 12.54 km from Chester

                      21

                      Sea Salt Beach House

                      Halifax Region / Queensland

                      Queensland boathouse

                      2 6 7 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 7 nights min
                      • Child Friendly
                      • Pet Friendly
                      • Private garden

                      Price per night from

                      $286

                      Price per night from

                      $286

                      Distance approx 10.79 km from Chester

                      (50) Excellent 

                        19

                        Hubbards/Halifax Oceanfront Home in Nova Scotia

                        Halifax Region / Hubbards

                        Hubbards house

                        3 6 min stay varies

                        • 3 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 10 mi
                        • Child Friendly
                        “Beautiful Views, Comortable and Relaxing Home” As you drive into the beautifully graveled driveway and see the ocean at the side of the house you just know that this will be a relaxing vacation. When you enter the house you are invited in by a well eq

                        Price per night from

                        $150

                        Price per night from

                        $150

                        Distance approx 9.87 km from Chester

                          14

                          Icicle

                          Halifax Region / Hubbards

                          Hubbards cottage

                          1 2 3 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 2 mi

                          Price per night from

                          $116

                          Responds fast!
                          avg. 1 hour 58 minutes

                          Price per night from

                          $116

                          Distance approx 18.24 km from Chester

                          (11) Very Good 

                            20

                            Rose Bay Cottage

                            Southwest Nova Scotia / Rose Bay

                            Rose Bay cottage

                            3 6 2 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 2 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 2 mi
                            • Child Friendly
                            “Delightful, whimsical little house by the sea” We have been coming to this cottage for several years and absolutely love it every time! It is a simple, relatively rustic house, but well laid-out, clean and organized. We have two young children, an

                            Price per night from

                            $300

                            Price per night from

                            $300

                            Distance approx 16.18 km from Chester

                            (5) Excellent 

                              18

                              A Seaside Loft Apartment Studio

                              Halifax Region / Glen Margaret

                              Glen Margaret apartment

                              1 2 3 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 3 nights min
                              • Beach / lakeside relaxation
                              • Nearest beach 16 mi
                              • Ask about children

                              Price per night from

                              $107

                              Responds fast!
                              avg. 6 minutes

                              Price per night from

                              $107

                              Distance approx 9.87 km from Chester

                              (1) Excellent 

                                15

                                Ice House Cottage

                                Halifax Region / Hubbards

                                Hubbards cottage

                                1 4 3 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 3 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 2 mi
                                • Private garden

                                Price per night from

                                $137

                                Responds fast!
                                avg. 1 hour 58 minutes

                                Price per night from

                                $137

                                Distance approx 15.2 km from Chester

                                (1) Excellent 

                                  9

                                  Oyster Cottage

                                  Halifax Region / Peggy's Cove

                                  Peggy's Cove cottage

                                  1 4 1 night min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 1 night min
                                  • Child Friendly
                                  • Air conditioning
                                  • Pet Friendly

                                  Price per night from

                                  $163

                                  Responds fast!
                                  avg. 43 minutes

                                  Price per night from

                                  $163

                                  Distance approx 15.2 km from Chester

                                  (1) Excellent 

                                    7

                                    Bluefin Cottage

                                    Halifax Region / Peggy's Cove

                                    Peggy's Cove cottage

                                    1 4 1 night min

                                    • 1 bedroom
                                    • sleeps 4
                                    • 1 night min
                                    • Child Friendly
                                    • Pet Friendly

                                    Price per night from

                                    $163

                                    Responds fast!
                                    avg. 43 minutes

                                    Price per night from

                                    $163

                                    Distance approx 12.04 km from Chester

                                    (4) Excellent 

                                    Certificate of Excellence

                                      13

                                      The Fox Lunenburg

                                      Southwest Nova Scotia / Lunenburg

                                      Lunenburg house

                                      3 6 3 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 3 nights min
                                      • Child Friendly
                                      • Pet Friendly
                                      • Private garden

                                      Certificate of Excellence

                                      Price per night from

                                      $86

                                      Responds fast!
                                      avg. 53 minutes

                                      Price per night from

                                      $86

                                      Distance approx 4.61 km from Chester Show on Map

                                      (1) Very Good 

                                        17

                                        Over The Way Cottage

                                        Southwest Nova Scotia / Western Shore

                                        Western Shore house

                                        2 5 3 nights min

                                        • 2 bedrooms
                                        • sleeps 5
                                        • 3 nights min
                                        • Nearest beach 25 mi
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $154

                                        Responds fast!
                                        avg. 2 hours 28 minutes

                                        Price per night from

                                        $154

                                        Distance approx 3.57 km from Chester Show on Map

                                          13

                                          Ocean View Updated Authentic Architecture Within view of Oak Island

                                          Southwest Nova Scotia / Western Shore

                                          Western Shore house

                                          4 8 min stay varies

                                          • 4 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Nearest beach 33 mi
                                          • Child Friendly
                                          • Private garden

                                          Price per night from

                                          $172

                                          Price per night from

                                          $172

                                          Distance approx 10.56 km from Chester

                                            10

                                            Halifax, Nova Scotia Oceanfront Vacation Rental

                                            Halifax Region / Halifax

                                            Halifax house

                                            4 10 7 nights min

                                            • 4 bedrooms
                                            • sleeps 10
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $580

                                            Price per night from

                                            $580

                                            Distance approx 19.66 km from Chester

                                            (1) Excellent 

                                              20

                                              4BR Cottage, Sweeping Ocean Views, Walk to Beach

                                              Southwest Nova Scotia / Riverport

                                              Riverport house

                                              4 8 3 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 3 nights min
                                              • Beach / lakeside relaxation
                                              • Child Friendly
                                              • Private garden

                                              Price per night from

                                              $343

                                              Price per night from

                                              $343

                                              Distance approx 18.34 km from Chester

                                              (5) Excellent 

                                                11

                                                Blue Heron Guest Home

                                                Halifax Region / Tantallon

                                                Tantallon house

                                                2 4 min stay varies

                                                • 2 bedrooms
                                                • sleeps 4
                                                • min stay varies
                                                • Nearest beach 22 mi
                                                • Child Friendly
                                                • Private garden

                                                Price per night from

                                                $193

                                                Responds fast!
                                                avg. 2 hours 24 minutes

                                                Price per night from

                                                $193

                                                Distance approx 15.38 km from Chester

                                                (1) Excellent 

                                                  17

                                                  Lakefront Cottage close to Sandy Beaches

                                                  Halifax Region / Boutiliers Point

                                                  Boutiliers Point house

                                                  2 6 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 1 mi
                                                  • Child Friendly

                                                  Price per night from

                                                  $176

                                                  Responds fast!
                                                  avg. 54 minutes

                                                  Price per night from

                                                  $176

                                                  Distance approx 4.96 km from Chester

                                                    26

                                                    Across The Cove Beach House

                                                    Southwest Nova Scotia / Western Shore

                                                    Western Shore house

                                                    2 4 5 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 5 nights min
                                                    • Nearest beach 25 mi
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $257

                                                    Responds fast!
                                                    avg. 2 hours 28 minutes

                                                    Price per night from

                                                    $257

                                                    Distance approx 11.25 km from Chester

                                                    (4) Excellent 

                                                      43

                                                      Tranquil Cove Near Lunenburg

                                                      Southwest Nova Scotia / Lunenburg

                                                      Lunenburg house

                                                      2 4 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 7 nights min
                                                      • Nearest beach 5 mi
                                                      • Private garden

                                                      Price per night from

                                                      $142

                                                      Responds fast!
                                                      avg. 3 hours 5 minutes

                                                      Price per night from

                                                      $142

                                                      Distance approx 11.24 km from Chester

                                                      (1) Excellent 

                                                        26

                                                        The Old Barn Blue Rocks - Lunenburg

                                                        Southwest Nova Scotia / Lunenburg

                                                        Lunenburg house

                                                        4 8 2 nights min

                                                        • 4 bedrooms
                                                        • sleeps 8
                                                        • 2 nights min
                                                        • Nearest beach 20 mi
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $133

                                                        Price per night from

                                                        $133

                                                        Distance approx 6.63 km from Chester

                                                          29

                                                          White Cape on the Cove - Year round ocean retreat!

                                                          Southwest Nova Scotia / Blandford

                                                          Blandford house

                                                          4 8 2 nights min

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • 2 nights min
                                                          • Nearest beach 6 mi
                                                          • Child Friendly

                                                          Price per night from

                                                          $167

                                                          Price per night from

                                                          $167

                                                          Distance approx 19.87 km from Chester

                                                          (16) Excellent 

                                                            21

                                                            East Coast Glamping Inc. Luxury camping holidays in Nova Scotia

                                                            Southwest Nova Scotia / New Germany

                                                            New Germany tented camp

                                                            1 5 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 5
                                                            • 2 nights min
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $171

                                                            Responds fast!
                                                            avg. 3 hours 50 minutes

                                                            Price per night from

                                                            $171

                                                            Distance approx 15.49 km from Chester

                                                            (12) Excellent 

                                                            Certificate of Excellence

                                                              15

                                                              Beachfront Cottage on Beautiful St Margarets Bay

                                                              Halifax Region / Boutiliers Point

                                                              Boutiliers Point cottage

                                                              5 min stay varies

                                                              • sleeps 5
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 2 mi
                                                              • Child Friendly

                                                              Certificate of Excellence

                                                              Price per night from

                                                              $171

                                                              Responds fast!
                                                              avg. 1 hour 42 minutes

                                                              Price per night from

                                                              $171

                                                              Distance approx 19.52 km from Chester

                                                              (16) Excellent 

                                                                33

                                                                Gladee's at Hirtle's Beach Lunenburg

                                                                Southwest Nova Scotia / Lunenburg

                                                                Lunenburg house

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Child Friendly

                                                                Price per night from

                                                                $129

                                                                Price per night from

                                                                $129

                                                                Distance approx 18.6 km from Chester

                                                                (1)  

                                                                  8

                                                                  Century Post Office

                                                                  Southwest Nova Scotia / Lunenburg

                                                                  Lunenburg cottage

                                                                  1 4 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 1 night min
                                                                  • Beach / lakeside relaxation

                                                                  Price per night from

                                                                  $132

                                                                  Price per night from

                                                                  $132

                                                                  Distance approx 9.44 km from Chester

                                                                    10

                                                                    Sea Side Shanty

                                                                    Halifax Region / Hubbards

                                                                    Hubbards cottage

                                                                    2 4 3 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 3 nights min
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $150

                                                                    Price per night from

                                                                    $150

                                                                    Distance approx 9.4 km from Chester

                                                                    (10) Excellent 

                                                                      28

                                                                      OCEANFRONT - Fish 'n Shells Cottage

                                                                      Halifax Region / Hubbards

                                                                      Hubbards cottage

                                                                      3 7 nights min

                                                                      • sleeps 3
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0 mi

                                                                      Price per night from

                                                                      $95

                                                                      Responds fast!
                                                                      avg. 39 minutes

                                                                      Price per night from

                                                                      $95

                                                                      Distance approx 8.82 km from Chester

                                                                        23

                                                                        Executive Ocean Front Estate with View of Waters of Mahone Bay

                                                                        Southwest Nova Scotia / Mahone Bay

                                                                        Mahone Bay house

                                                                        5 10 min stay varies

                                                                        • 5 bedrooms
                                                                        • sleeps 10
                                                                        • min stay varies
                                                                        • Nearest beach 7 mi
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $368

                                                                        Price per night from

                                                                        $368

                                                                        Distance approx 4.62 km from Chester Show on Map

                                                                        (5) Excellent 

                                                                          22

                                                                          Far Far Away Guesthouse

                                                                          Southwest Nova Scotia / Mahone Bay

                                                                          Mahone Bay cottage

                                                                          1 3 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 3
                                                                          • 3 nights min
                                                                          • Nearest beach 25 mi
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $129

                                                                          Responds fast!
                                                                          avg. 2 hours 28 minutes

                                                                          Price per night from

                                                                          $129

                                                                          Distance approx 15.17 km from Chester

                                                                          (5) Excellent 

                                                                            14

                                                                            Ocean View Cottage

                                                                            Southwest Nova Scotia / Lunenburg

                                                                            Lunenburg cottage

                                                                            4 8 5 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 5 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Ask about pets

                                                                            Price per night from

                                                                            $214

                                                                            Price per night from

                                                                            $214

                                                                            Distance approx 18.56 km from Chester

                                                                            (1) Excellent 

                                                                              14

                                                                              Character ocean view cottage with spectacular view

                                                                              Southwest Nova Scotia / Riverport

                                                                              Riverport house

                                                                              3 8 4 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • 4 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $214

                                                                              Price per night from

                                                                              $214